Neither of these two strategies are "socialist" or "capitalist"; complete misuse of those two terms.

You don't see the similarity?

Granted, the metaphor has nothing to do with property rights, taxation, or market regulation, but it's meant as a simplified analogy, not a facsimile. If central planning is present in "socialist" theory/practice, and if individual economic autonomy is present in "capitalist" theory/practice, then the use of the terms is correct, and the analogy is apt.

Central planning is essential for large scale projects like railroads and highways. It was also used for postal service and telecommunication. A monopoly can be privately owned, but still government regulated. American companies are pretty heavily regulated because prior to regulation, they fouled both the natural and social environments and repeatedly crashed the economy. American businesses responded by moving their operations elsewhere.

We sort of know where central planning is needed and where competition is best.

Except all instances of free market Capitalism have been centrally planned, and central planning doesn't necessarily preclude the opportunity for individual autonomy. In some respect it may be it's precondition. So I don't see the analogy having historical or theoretical legitimacy. It's a false dichotomy.

Except all instances of free market Capitalism have been centrally planned — Maw

In many ways individual autonomy and central authority are incompatible. Free markets might require some central authority to support, stabilize, or insulate them, but the markets themselves work because of the autonomy that individual entities possess. Many aspects of our society are centrally planned, and many aspects rely on the benefits of free markets; my reference to capitalist and socialist theory and practice might generalize complex spectra, but the broad and general point I'm making still stands:

There is no universal strategic principle or theory that can solve all problems; strategies should be informed and formulated according to the specifics of different situations. The best we can do is suppose the statistical likelihood of risks and outcomes, which is always limited by our ability to detect and compute unknown variables, especially given potentially vast circumstantial differences between individual cases (which we seldom have the time or interest to investigate thoroughly).

I feel like you're getting a bit too hung up on the comparison to capitalism and socialism. Sure, they could centrally plan their boat construction while each deciding their own direction, but the dilemma pertains to the single decision of whether or not to all head out in the same direction. It's a yes or no proposition; there is no third option.

Central planning is essential for large scale projects like railroads and highways — frank

But for other large scale endeavors it can prove ineffective. I would say that generally, the greater the scale, and when there are more unknowns, the more difficult it is for central planning to cope with the various logistical demands of large complex systems. But if partial failure (inherent in free market principles) is not acceptable, then relying on markets tends to become less attractive.

The funding and execution of scientific research is an interesting example. At present, a combination of government and private funding drives ongoing research in different areas which are determined by a combination of market forces and planned initiatives. Specific academic entities and operations/endeavors themselves have a mix of central planning and internal autonomy that serves their purposes/needs, and globally they form a marketplace of scientific knowledge and research potential. Without that marketplace, our ability to innovate would be hamstrung, but without some regulation (e.g: nuclear research, bio-ethics, etc...) we would be courting too much risk. Knowing the optimal strategic mix can only be determined with experience of a given situation.

We sort of know where central planning is needed and where competition is best. — frank

Sort of, I agree. But we too easily conflate strategic success in one situation with the universal applicability of the successful strategy.

An interesting way to conceptualize the problem. I like your approach. It's certainly true that the discussion between capitalism and socialism, or perhaps individualism and communalism, is too much driven by ideology.

There is of course the issue that "free market" is a fundamentally contested term. We know what the free market model is, but not what actually defines a free market as an economic system. We have capitalist economic systems with a market economy, is that the same thing as a "free market"?

This is where the application of metaphors runs into a problem. Why is central planning represented by few, large boats when the central plan might just as well be to send out many small boats? And if individual preference is central to the free market, isn't it plausible that individuals might prefer to all stick together, for better or worse?

We'd first need to identify what, exactly, a free market is about and what the other alternatives are.

In the thought experiment, especially given the stipulation that no one knows where land is, I think the best approach would be a bunch of small boats, but where (a) we systematically determine the basic exploration vectors each boat will take, (b) our best navigator, etc. teaches everyone (as much as possible in the time available) navigation skills, etc., and (c) part of the strategy is to come up with an additional exploration plan for survivors to try to contact others in the future, to enable future cooperation, where we can take advantage, for everyone, of what we've discovered.

Per other comments above, I also think this isn't a very good analogy for the free market versus central planning dichotomy, for a number of reasons, including that free markets enable competing with others in a manner that you can "win" by doing things to make certain others lose. I think it's better to make the competition so that you win the most by helping others win, too. The competition should be how to best ensure that everyone's lives are better/easier/etc.

But for other large scale endeavors it can prove ineffective. I would say that generally, the greater the scale, and when there are more unknowns, the more difficult it is for central planning to cope with the various logistical demands of large complex systems. — VagabondSpectre

Could you give an example? I think we have all sorts of expertise at logistics. I think the main flaw in central planning is that it usually requires dictatorial authority. Without enough checks on power, the danger is idiots like Khrushchev who guided his nation to disaster, one stupid decision after another. A free market has nature as the check on stupidity.

But we too easily conflate strategic success in one situation with the universal applicability of the successful strategy. — VagabondSpectre

True. That's politics, though. People pour all their fear and belligerence into it. The truth is we have extravagant demonstrations of the folly of embracing either route single-mindedly. It doesn't matter. We have a limited ability to learn from our mistakes.

The OP's question does have a logical alternative.

Yes, every family makes boats, but as the trip to the unknown will definately be extremely dangerous, the most able boat builders should supervise the building of the boats and the most able seamen should supervize (and teach skills) that the people have at least the thin possibility of making it and have enough seamanship to survive in the ocean. Having inferior the boats sink in front of the island wouldn't be nice.

Hence the juxtaposition between "free market" and "central planning" isn't a great question as the mixture of both have in history been the most successfull: basically as a free market cannot operate well without institutions (contrary to the silly brainfarts of anarcho-libertarians) and on the other hand central planning cannot be successfull without some freedom of invention and innovation (as obviously central planners cannot know what the future holds and what will be successfull).

This is where the application of metaphors runs into a problem. Why is central planning represented by few, large boats when the central plan might just as well be to send out many small boats? And if individual preference is central to the free market, isn't it plausible that individuals might prefer to all stick together, for better or worse? — Echarmion

Free markets and centrally planned systems are somewhat handy ideology-laden real world examples that vaguely parallel the dilemma, but my real point of interest is with an aspect of "strategy" itself (how we confuse it with truth):

We formulate strategic principles as predictive tools, and the very useful ones we retain and sharpen over time (in hopes of cross-application; utility), but we often don't recognize that the utility of a given strategy depends entirely on how well it accommodates the specifics of a given situation. When we lack access to certain data in a given circumstance, we may have no way of discriminating between two different strategic options (or finding the optimal mix of both).

Political, economic, and ethical schools of thought are filled to the brim with predictions derived from strategic principles, but every time they are applied to a novel situation (instead of deriving the strategy from the novel situation), there's ultimately some degree of fallacy in the presumptive appeal that what works in one situation will work in another.

Forget about the boat building and navigation, and assume everyone has their boats ready to go, and that a final decision must be made. Should people head in different directions or should they keep together? If there's no way of knowing which direction is best, then the ratio of risk to reward seems to stay constant no matter what strategy or directions they choose. It's like putting all your money on a single number in roulette Vs spreading it out with many smaller bets on many different numbers.

Regarding free market and central planning specifically (capitalism/socialism, informally), the best laid arguments compare present circumstances to historically observed circumstances, but more often than not pundits and politicians are hastily and haphazardly applying the same political/economic answer to every new question (and we the body politic lap it up). As you say, our political [and moral] discussions are largely driven by ideological adherence to what amounts to a strategy.

We're biased toward the strategies we're most familiar with, even when we might have no rational cause to favor them in a novel situation. Instead of treating our predictive strategies as specific tools for specific problems, somehow we start pretending that they're universal truths.

Per other comments above, I also think this isn't a very good analogy for the free market versus central planning dichotomy, for a number of reasons, including that free markets enable competing with others in a manner that you can "win" by doing things to make certain others lose. I think it's better to make the competition so that you win the most by helping others win, too. The competition should be how to best ensure that everyone's lives are better/easier/etc. — Terrapin Station

If we focus only on the decision of whether or not to head out in different directions, there's really no way of stipulating what is best. I was hoping that this dilemma would show that the predictive power of strategic principles can be entirely determined by the circumstances they are to be employed in (where unknowns can render strategic decision making impossible), but I left too much room for the imagination by adding boat construction and navigation to the mix.

Choosing one direction/choosing many directions was meant to parallel with basic central planning/free market principles, not capture them entirely.

Could you give an example? — frank

The best example is also probably the most broadly useful principle/effect of free markets: determining the value of things; setting prices. As markets and economies grow, they become exponentially more complex and interconnected. Allowing prices to emerge and self-correct naturally from markets is not risk free or perfect, but it tends to produce useful approximates. The more and more complex relationships a specific good or service has with the greater system, the harder it would be for a central planner to successfully set the value of that good or service.

That's politics, though. People pour all their fear and belligerence into it. The truth is we have extravagant demonstrations of the folly of embracing either route single-mindedly. — frank

:up:

the mixture of both have in history been the most successfull: basically as a free market cannot operate well without institutions (contrary to the silly brainfarts of anarcho-libertarians) and on the other hand central planning cannot be successfull without some freedom of invention and innovation (as obviously central planners cannot know what the future holds and what will be successfull). — ssu

This kind of shows the overall point I'm trying to make: there's no strategic panacea; no fool proof ideology. Not only has a mixture of both been most successful, different mixtures at different times have been most successful.

I guess what I wanted from this thread is a way to show proponents of political, economic and moral strategies, that given a change in circumstances or available information, their lofty convictions might amount to nothing.

The flotilla of boats is evolution, the seeds dispersed, because the future exists. Less risk of the idea dying.

The single boat is God’s world, one idea; we all get through or none of us do. There is no future, there is only now. Greater risk in terms of the flotilla’s view, but no risk in the eyes of the single boat.

This guy gets it!

Your analogy is self contradictory.

Allowing everyone to build their own boat will almost certainly result in some death, but it has a much higher chance of saving at least some lives. — VagabondSpectre

Contradicts:

Without knowing something more about the situation, there's no good way decide which strategy is superior — VagabondSpectre

We do have information, which is some small boats have a much higher chance of some people surviving.

Predicting which strategy is superior is impossible without knowing more about the circumstances of the situation and environment. — VagabondSpectre

If the goal is to make sure at least some people survive (to carry on the culture, tell the story) then we already do know that the small boats strategy is best, since you have specified that some small boats have a much higher probability of some to survive: strategy done.

The only reason to change strategies is if the goal is different: for instance people want to "survive as a group or sink as a group", in which case the big boat is the only choice in your scenario, as you also specify that some people in the small boats would certainly die.

In the real world, we wouldn't know if some small boats would be essentially guaranteed to survive. It could be all the small boats sink, and the big boat (more stable, more hands, more volume and resources per person) has a better chance of surviving even compared to a single boat of the flotilla. It would depend on their sailing skills and experience, which you postulate they do have; beyond that, depends on the goal.

If they value "the idea surviving" as Bret assumes they do, then it's whatever results in the highest probability of anyone surviving, which you simply specify the small boats have a better survival chance; so problem solved. If they have little concept of a "wider humanity" for their idea to contribute to, they may not see any value in a single boat surviving but only the community as a whole.

With the high taxes, crippling regulations, need to build 37 bathrooms (one for each gender) and designated “safe spaces” on each deck of the ship, etc etc, the lava would be knee high before the socialists could launch even one ship.

With the high taxes, crippling regulations, need to build 37 bathrooms (one for each gender) and designated “safe spaces” on each deck of the ship, etc etc, the lava would be knee high before the socialists could launch even one ship. — praxis

What elements of the scenario do you base these conclusions?

The scenario seems to be constructed that each have an equal "expected return" of people surviving, but a different expected return on anyone at all / the culture surviving. The scenario then posits the people discuss the two options but without relation to what their collective goal is.

A better free market analogy is that the choice is between the two centrally planned decisions (when Cesar had his men build a bunch of ships to cross the Adriadic instead of one big ship, this was still centrally planned, just so happens a certain size ship was considered optimum), on the one hand, and on the other a truly free market where people can only use their existing wealth to build ships for themselves or for sale, and that the people that do not own an ax nor any land and cannot build any ships are kindly requested to labour in return for food (or the market rate, if it's slightly more then some, if they labour enough, may even afford a little raft of their own some day) if offered by the people that do have wealth and are also kindly requested not to make a fuss about likely being left out entirely of any benefits society may generate with this approach. The people with wealth would then more effectively allocate those resources to try and save themselves, than some central planner simply mandating a given number of ships be built, regardless of whether it is 1 or several, and appropriating Private Land and Privately Owned Trees to fulfill that mandate. However, if the poor people do make a fuss and cause conflict, then this would lower the odds of surviving for those that do have the resources to build ships. The poor are just moral degenerates if they do that and will need to be dealt with for their attempt to overthrow the social order and steal resources from those that have worked hard to accumulate them prior to the disaster for the benefit, among other things, of being more able to survive in a disaster.

I'm disappointed that no one is arguing for the free-market solution I propose to the problem: of letting people act with their own wealth, as it is my understanding the point of this thread was to contrast free market principles and central planning principles in this example.

There's clearly the conditions of a market with specialization of at least shipbuilding and sea fairing skills. By allowing people to use their existing wealth to meet this problem the way they see fit, this no only creates a diversity of solutions but also ensures survival is heavily weighted towards the "wealth creators", which, we can presume based on no evidence, are the kinds of people that can best reboot their society wherever they land. Now, of course there will be less people on boats overall compared to one of the central planning options proposed by the OP, But, private property will be respected in the free market scenario and thus more moral if we assume private property is moral bedrock of society, so what would be hypothetically more effective doesn't matter if we take this view.

However, as alluded to in my previous post, people who will be left to die may get angry. My question is what is the optimum way to deal with such anger to ensure the market runs efficiently and doesn't interfere with the efficient boat building of those with wealth?

We do have information, which is some small boats have a much higher chance of some people surviving. — boethius

But the trade-offs are not known or are presumed to be equal. Some boats means it is more likely that at least some people will survive but makes it more likely that some people will die, but the big boat makes it much more likely that everyone will survive and more likely that everyone will die.

If you're an individual who wants the best shot at staying alive, then you probably want the big boat. If you're someone who wants to ensure the continuation of the society and culture, then you want the small boats. Most people probably don't know which they would actually choose.

The strategic dilemma emerges precisely because we have two different strategies but we don't know which one is optimal. By establishing broad goals (long term survival of the genome vs short term survival of individuals) we can fathom which option is better, but we still don't know if the decision we end up making will be the best one. If people disagree about the importance of individual vs group survival, then there's no way to select a mutually acceptable strategy; because we're ignorant of what is to come, at some point, to some degree, we're just flipping coins or rolling dice in the very selection of our strategic methods.

I'm disappointed that no one is arguing for the free-market solution I propose to the problem: of letting people act with their own wealth, as it is my understanding the point of this thread was to contrast free market principles and central planning principles in this example. — boethius

The purpose of this thread was to put one of these strategic coin-flips front and center, the strategic dilemma I chose was only meant to facilitate the example (in hindsight, I focused too much on free markets vs central planning).

The strategic dilemma emerges precisely because we have two different strategies but we don't know which one is optimal. — VagabondSpectre

Optimal for what purpose? Optimization requires a specific objective. So, the optimum strategy will depend on what the objective is. If you do not adequately specify the objective, then the term optimum is not applicable. Your example simply shows why optimization is tied to objective, there is no "optimum in a vacuum".

It's like if I hand you a chair and I say "is this optimum? if not, optimize if for me", you cannot achieve any optimization without knowing (or then speculating) as to my objective with the chair.

If the community is trying to ensure survival of the community as a whole, and so weights more favorably a plan that has a higher probability of "everyone surviving".

If you're an individual who wants the best shot at staying alive, then you probably want the big boat. If you're someone who wants to ensure the continuation of the society and culture, then you want the small boats. Most people probably don't know which they would actually choose. — VagabondSpectre

I agree. What is seen as optimum will be determined by what people's objectives are.

For instance, if the sailors just want to maximize their own survival they may decide the optimum strategy is to build an optimum sized boat for themselves in secret (while pretending to do whatever society decided) and just cast off in the night. Obviously, if they wanted to maximize the survival of others they would never consider that plan (unless, they decide it's become the only plan that will potentially save anyone).

The purpose of this thread was to put one of these strategic coin-flips front and center, the strategic dilemma I chose was only meant to facilitate the example (in hindsight, I focused too much on free markets vs central planning). — VagabondSpectre

You were pretty clear your purpose was to discuss the scenario as an analogy of a free market principle vs central planning principle.

If you want to explore the factors you discuss in your latest post, I have zero qualms. It is an interesting situation, and more followup questions could be asked such as "small boats will save at least 5% of people with 95% chance, but the large boat will save everyone with 70% probability". Even someone that values survival of the culture more may have a cutoff point.

However, the organizational principles you are discussing are not free market vs central planning, but decentralization vs centralization in terms of engineering and devolution of responsibility vs hierarchical management in terms of organizational principle.

As other posters have noted, these principles cannot be resolved in the abstract. For instance, already an engineering example was mentioned of rail building; if you want to make a rail line you can't divide your workforce up into small groups who can all design their mile track as they want and built it where they want; there maybe some innovation in this scenario but zero return on investment in this rail line.

An example of devolution vs hierarchy, is that in a jungle war, devolving command to small platoons that can take their own initiative, do things in their own way and often self-organize with spotty coordination with other platoons and the generals hut, can be optimum; but small groups with spotty coordination wandering around an aircraft carrier is probably not what the captain will choose.

Free market proponents only loosely appeal to devolution and decentralization as supporting principles. Although they certainly don't like centralized micro-management of bureaucratic central planning, they don't mind centralization of production and strict command hierarchies used in large corporations (if the shoe fits). If a corporation succeeds pushing the limits of centralization and hierarchy, then obviously it was a good strategy in this case. Likewise, even for government, when trade requires central bureaucracy and planning (laws, standards, finding pirates, trade treaties and international trade organizations like the WTO) free market proponents are generally supportive (of course, any given law, standard or treaty, they may object to on other grounds), and if local structures attempt to assert local control (use wherever devolution of power they have, or try to get more for the purpose) in a way that would obstruct production of good or trade (for instance, banning fracking on the land overseen by this local political body), then free market proponents are usually supportive of using hierarchy to stop application of devolution of responsibility.

However, to have an analogue of a market economy, there must be private property and actors exchanging goods and services; to have a "free market economy" (as usually understood by self-identified free-market proponents, at least in the US), there is usually the principle that failing to compete and gain wealth should not be rewarded by other people's taxes, directly nor through programs like education and healthcare (or there are no taxes to begin with in some schemes), and there is usually a heavy dose of "deregulation" (but I have never seen a formulation of deregulation that does not reduce to "I want to get rid of rules I don't like ... but hold on, don't get rid of the rules I do like!"; but I'd be interested to meet one).

The point of my third strategy is to point out you can have a free market in your scenario: everyone relying on their own wealth and trading and selling to achieve whatever strategy they personally think is best for themselves. If you agree it's absurd to rely on a free market economy to solve the problem in your scenario, to the point it won't even occur to most people, I agree.

Adherence to socialist or capitalist principles, like choosing a strategy for the survival of you or your tribe, is a gamble (a wager that following X principle will tend to lead to individual or overall success). — VagabondSpectre

Arguments against "planning", in the economic sense, are made in the "tribal" register used in your narrative. Hayek, for example, was not a Libertarian on the basis of saying restrictions upon individuals were bad upon principle but that it stifled productivity of the whole process. The language Hayek used developed to the point where the Reagans (he was cloned repeatedly) argued that the free market was the only guarantor of beneficial social ends.

And so what started off as an argument about governmental involvement in the production and the marketing of goods became a view that all functions of government would be better served by commodities developed through a market environment. Resistance to that movement argues that forms of civic planning may be the only way to protect individuals from the unrelenting demand of being a consumable commodity.

Kind of ironic, really.

I think that your analogy is much more indicative of centralized vs dispersed societies than economic systems, but it's still a good analogy.

One thing I struggle with in considering political ideologies is that they all face the pitfalls of one strategy or the other. Yes, I want individual autonomy, but not at the expense of the higher standard of living and broader range of experiences offered by a centralized society. Yes, I want a higher standard of living, but not at the expense of my ability to pursue self-actualization.

Ideally, there would be some tertiary option where a fleet of small boats travels together in the same direction, sharing resources, but all are able to break away if they don't agree with the main group's heading. The real world equivalent would be a society with the benefits of centralization, but where smaller groups or even individuals can opt out of the social contract. The closest example I can think of is the early US, where the disillusioned could just head west to the frontier. Besides that, it's more wishful thinking than a realistic proposition.

Optimal for what purpose? Optimization requires a specific objective. So, the optimum strategy will depend on what the objective is. If you do not adequately specify the objective, then the term optimum is not applicable. Your example simply shows why optimization is tied to objective, there is no "optimum in a vacuum".

It's like if I hand you a chair and I say "is this optimum? if not, optimize if for me", you cannot achieve any optimization without knowing (or then speculating) as to my objective with the chair.

If the community is trying to ensure survival of the community as a whole, and so weights more favorably a plan that has a higher probability of "everyone surviving". — boethius

Agreed, but even when we establish an objective we can still have no way to discriminate between strategic options.

Consider a roulette wheel. Your objective is to walk out of the casino with as much money as possible. Do you bet your only dollar on red/black, or do you bet it on a number? They have the same ratio of risk to return, and you only have enough money for one initial bet. Which option do you choose, and why?

I agree. What is seen as optimum will be determined by what people's objectives are.

For instance, if the sailors just want to maximize their own survival they may decide the optimum strategy is to build an optimum sized boat for themselves in secret (while pretending to do whatever society decided) and just cast off in the night. Obviously, if they wanted to maximize the survival of others they would never consider that plan (unless, they decide it's become the only plan that will potentially save anyone). — boethius

This is more or less why I hoped the analogy would be an effective metaphor for my point about strategic ambiguity. There are 1000 possible unknown factors that influence efficiency on a granular level such that we just don't know which option is best for each individual, or each set of individuals.

You were pretty clear your purpose was to discuss the scenario as an analogy of a free market principle vs central planning principle. — boethius

Well yes, but aren't I allowed to have underlying intentions? :)

The final sentences of my OP's paragraph frame the understanding I sought to impart:
"Adherence to socialist or capitalist principles, like choosing a strategy for the survival of you or your tribe, is a gamble (a wager that following X principle will tend to lead to individual or overall success). The best we can do is suppose the statistical likelihood of risks and outcomes, which is always limited by our ability to detect and compute unknown variables, especially given potentially vast circumstantial differences between individual cases (which we seldom have the time or interest to investigate thoroughly).

The bold is meant to actually apply to all possible strategic dilemmas. The very best chess player (or computer) on earth simultaneously makes the most well informed decision that anyone can possibly make, but they're still confronting and accepting some degree of risk given the inevitable unknowns.

Free market proponents only loosely appeal to devolution and decentralization as supporting principles — boethius

Their appeals might be loose, but they're damned frequent, especially in the neo-conservative from the camps (absolutely everything would be privatized if they had their way).

My hope was that in understanding the limits and ambiguities of strategic decision making, I could inoculate people against dogmatic subscription to one particular strategic regime.

The point of my third strategy is to point out you can have a free market in your scenario: everyone relying on their own wealth and trading and selling to achieve whatever strategy they personally think is best for themselves. If you agree it's absurd to rely on a free market economy to solve the problem in your scenario, to the point it won't even occur to most people, I agree. — boethius

I think with most things it's a mixture of bottom up and top decision making that produces the most robust results, but depending on the actual circumstances, we may be better off centralizing or decentralizing different aspects of our collective and individual decision-making.

Agreed, but even when we establish an objective we can still have no way to discriminate between strategic options. — VagabondSpectre

Yes, in terms of strategy, two plans can be equal, and a coin flip can be a convenient method to decide.

For instance, if you build a chess program to find and play the best move it can, if there are two moves that seem equal (which is common both at the start of the game due to being unable to calculate every variation, but also at the end of the game it is common that there are several ways to checkmate in the same amount of moves), it takes little thought to just add some random way to make the move.

There's not much philosophical controversy about some options being equivalent.

Some take the existence of such choices, whether in chess or the choice between shirt colours, as indication that all choices resolve to preference, but as soon as we remember that there's always third choices like "jumping out a 10 story window" it's fairly clear that the mere existence of equivalent decisions doesn't somehow imply all choices are equal (if we've decided we need a shirt in our plan, this is already a very constrained set of actions compared to everything we are motor-capable of doing; indeed, our whole framework of talking about "choices" and "decisions" already excludes the vast majority of options that are available but have no coherent description).

This is a tangent to your inquiry, but criticism of preferentialism may be of related interest to you.

If your interest is in resolving what seem like equivalent choices, there is plenty of subject matter. Such as to what extent preferences can justify decisions, on what basis to treat two options as equivalent compared to the potential of further analysis uncovering a difference, as well as just decision making in general.

However, since you state your purpose as comparing, or building up some elements for the purposes of comparison, central planning vs free market then it's required to step back a little.

Free market proponents may not have the same goal, and so talking about efficiency can serve to distract people into a debate framework that has no resolution as no objective has been specified. In particular, free market proponents state that it's each individual following their own interest (after a vaguely defined participation in a common interest to maintain institutions that enforce property rights) is what's best for the people with property (they may say "best for society" but this always reduces to "people with property").

Most importantly, (beyond a vague duty to collectively enforce property rights) free market proponents generally deny that society can have any collective objective, that all objectives are personal. So, in a free market framework, the question of "what best for the island society" is not a recognized question (there is no society, only individuals). So, what matters is the objectives of the individuals; if individuals was to help save family and friends with their property that's their prerogative, and if they want to "get out ahead" either alone or in covert cooperation with the other best abled people and leave everyone else to die, that would be their prerogative too. In both cases, free market proponents would try to argue that the outcome was the most efficient, either people freely providing charity to help others or then the weak and pathetic getting purged and the strong have survived. It's just evolution. Of course, everything that happens is part of evolution, so if our founding principle is some sort of evolutionary social darwanism, then everything in retrospection is effecient because it is the result of an evolutionary process because it happened.

Consider a roulette wheel. Your objective is to walk out of the casino with as much money as possible. Do you bet your only dollar on red/black, or do you bet it on a number? They have the same ratio of risk to return, and you only have enough money for one initial bet. Which option do you choose, and why? — VagabondSpectre

Again, you are missing the third choice available which is to bet the minimum required to fulfill your scenario and then walk out, precisely because the expected returns of all betting strategies for roulette are equivalently bad; therefore, if the objective is to walk out with as much money as possible then simply walking in and walking out with the money you came in with is the best option. The only thing that would change this is if you are in some situation where a negative expected return is the best option for extraneous reasons: for instance gangsters will kill you in half an hour with the money you have or no money, and the best option available is to try to double your money at roulette; in which case flipping a coin for red or black and placing all your money down I think would be recommended by most mathematicians (you'll still have 25 minutes to try and run if you lose).

Well yes, but aren't I allowed to have underlying intentions? :)

The final sentences of my OP's paragraph frame the understanding I sought to impart:
"Adherence to socialist or capitalist principles, like choosing a strategy for the survival of you or your tribe, is a gamble (a wager that following X principle will tend to lead to individual or overall success). The best we can do is suppose the statistical likelihood of risks and outcomes, which is always limited by our ability to detect and compute unknown variables, especially given potentially vast circumstantial differences between individual cases (which we seldom have the time or interest to investigate thoroughly). — VagabondSpectre

Yes, this is exactly the mistake I am trying to elucidate. You are assuming market adherents have the objective of the survival of their tribe or humanity as a whole. Free market adherents do not have this goal. If they are cornered and forced to accept scientific evidence that ecosystems are in trouble largely due to market driven consumption, they will retreat to either an assumption that these problems will be solved by the market by future innovations (that there is zero value in any mitigating strategy, not because proper risk-analysis indicated going "all in" with presuming future innovations will solve all problems but because their real goal is maintaining property rights and investor value, in other words the status quo) or they will say future generations don't matter (we need not care about them, they are outside our interests by definition and it's just weak morals to care) or they will say things like "life will survive" (evolution, see below) with an honest belief that proposing we destroy civilization and most complex life is simply a suitable outcome for our endeavors (though really they will simultaneously believe all three, and consider the adoption of three incompatible justifications for the same position is strength in numbers and good thinking).

Their appeals might be loose, but they're damned frequent, especially in the neo-conservative from the camps (absolutely everything would be privatized if they had their way). — VagabondSpectre

By "loose" I am referring to the inconsistency of those appeals. In their propaganda, there is a large stress on personal autonomy, because all the institutions that are needed for their vision of society already exist: police, law, corporations, land and other property rights, integrated transportation networks.

However, if they really believed in devolution and decentralization, they would be for a principle of maximum autonomy of local and municipal government, and would totally fine if a local government banned fracking or any other activity on or crossing their land, and had also the power to appropriate anyone's land for whatever purpose having maximum sovereignty over their purview. Neoconservatives would of course be horrified by such an argument based on devolution of responsibility, and indeed whenever local government do anything that would harm corporate interests (protect small business, protect their environment, etc.) neo-conservatives are the first to propose state or federal laws that ban such local exercise of autonomy.

Knowing this, when discussing with a more sophisticated interlocutor they try to remold their arguments in terms of balance and optimization between these principles. However, they cannot say who they are optimizing for (as they only believe in personal objectives, no social objectives), so their arguments make no sense, but they sounded "intellectual" and so the real objects of their dissertations (people who are unsophisticated enough in their thinking to vote against their own interests) are left non-the-wiser.

However, discuss enough and you will discover their only consistent principle is private property; every other principle they will cast aside as soon as it conflicts with private property. So, the reasonable conclusion is that their objective is to maintain property rights, and, in the pursuit of this objective, it is a good play to claim this will benefit society as a whole always, and if defeated in any of these claims simply fall back to property rights being a moral issue and not a social objective issue (which, again, they can't formulate to begin with because only individuals have goals and they don't know the goals of all individuals, except that everyone supports property rights or at least enough of them and if they don't then they are morally incorrect and whatever their interests are should be ignored).

I think with most things it's a mixture of bottom up and top decision making that produces the most robust results, but depending on the actual circumstances, we may be better off centralizing or decentralizing different aspects of our collective and individual decision-making. — VagabondSpectre

Yes, we agree on the framework, but what I hope I've drawn your attention to is that differences in objectives have very deep consequences.

Intellectuals, who think about the future of humanity, like to assume everyone shares the objective of our collective survival, this is not the case. For instance, you will often hear better defenses of neo-conservative by intellectuals that aren't neo-conservatives due to this erroneous belief that they must truly believe their policy objectives are good for everyone and that if parts make no sense from this point of view it must be an honest or cultural mistake. However, it's easy to verify that this "good for everyone" objective simply isn't there. For instance, when neo-conservatives pass laws privatizing public land, even if it's proven by an economist that it's simply not a good business deal for society, this doesn't change their position in anyway and they will try to avoid any such calculation of what the land is worth to society being made in the first place.

Of course this doesn't cover all libertarians; some like the label, don't see a problem with homosexuals or Hispanics and like weed but don't like pointless wars or taxes and want to support the conservative for this tax reason while being able avoid any questions about de facto supporting all the other conservative positions (and so an ideology that has recast taxes as the devil fulfills this roll of being able to ignore all other implications of voting conservative but still "feeling intellectual" and principled about it).

Libertarians that are intellectually curious and concerned about humanity, in my experience, are generally young men persuaded by "useful idiots" that appear on television and seem intellectually respected (as their television appearances are designed to give this affect), and if they stay libertarian it's for tribal group reasons, but they must make so many exceptions to the TV neo-conservative starting point to deal with all the issues (public institutions cannot be maintained by a system of private greed, people voting for their interests which may conflict with elite property interests, there's no reason to allow costs to be externalized, things like child education and firemen do have a public utility and there's no fundamental reason not to expand such public institutions, market failures, corruption etc.) that making all these exceptions really produces a different theory (social democracy of Scandinavia) but they still don't want "that many taxes" so they stick with libertarianism as at least a slowing force to obvious truths.

And, there are some libertarians trying to be truly intellectually consistent with no exceptions, and they end up in places like "anarcho-capitalism" and "seasteading" and view the state (that cannot exist without taxes) as the devil's master; but, I'm not too interested to debate them as they are politically irrelevant and have no theory of government at all (but it's an easy task when the ocassion arises).