The move to the unconditioned is not made by upgrading epistemic necessity into modal necessity, It is made by reflecting on what judgment itself presupposes in order to be truth-apt at all. — Esse Quam Videri
So what I'm looking for in your response is "what judgment itself presupposes" so that a judgement can be true or false.
If our operating notion of reality were such that reality is conditioned all the way down, then for any claim, further conditions could always be demanded such that no fact, state of affairs or claim could ever be counted as truly settled. — Esse Quam Videri
Is this concerning the branch of Agrippa’s trilemma that results in an infinite regress? Ok.
This is not the same as saying merely that we are finite and fallible, or that inquiry is ongoing. It implies something much stronger - namely, that there is no fact of the matter that could ever settle a judgment as finally correct, because any purported settlement is always relative to a context, stage or set of conditions that could always, in principle, be revised. — Esse Quam Videri
So your trilemma is set up like this, using the language you are adopting: we suppose that if someone judges something to be true then they are able to state the conditions under which they so judge; but then they must either again explain their judgement as to the truth of those conditions; or they must take them as fundamental; or they must rely on circularity, where judgements form the conditions for themselves.
And the conclusion is that "...no fact of the matter... could ever settle a judgment as finally correct".
You then spend a few paragraphs explaining much the same thing for negation. If someone were to deny that water is H₂O, we would never be in a position to say in some absolute sense that they are wrong, because there would always remain some conditions that are not judged to be true... or something along those lines. We could never say their denial is wrong...
One might respond “Okay, maybe ‘final truth’ disappears, but why does ordinary truth go with it?”. The robust notion of truth implicit in every act of judgment is not just “what we currently accept”, “what fits in a framework” or “what is best so far”. Implicit within the robust notion of truth is the idea that “this is how things really are, and denying it misrepresents reality”. But if reality itself is understood to be such that it can never settle anything without remainder, then the very notion of “misrepresenting reality” has no determinate content, and the robust notion of truth itself becomes indistinguishable from provisional endorsement. — Esse Quam Videri
So now you have two notions of truth, ordinary and robust. Ordinary truth is "what's best so far" and robust truth is "how things really are". You worry is about losing the ability to tell which we have.
But this is not an apt characterization of what we are doing when we engage in authentic inquiry. The way we talk about such things betrays the fact that the very act of judging each other's claims to be true or false carries within it an implicit commitment to robust notions of truth and reality and, thus, to reality itself being unconditioned (and intelligible) without remainder. — Esse Quam Videri
So now you have along side the two notion of truth, two notions of explanation, one of which is "authentic" in that it commits one to saying how things are "unconditionally".
Now I think your have drawn yourself a nice picture here of how you think epistemology works, but that there are fundamental problems in the way that this picture has been set up that lead you to a sort of absolute conclusion that is erroneous.
Let's start with an example. I think that if I ask you if you are reading this post, here, and now, you would quite rightly judge that you are. Now on your account, since you so judge, there must be "conditions" for that judgement. And the condition for it being true that you are reading this post, here, and now is just that you are reading this post, here, and now. So here, the condition and the judgement are the very same.
I'm not suggesting that your judgement is based on some
observation of yourself reading, but that what you are now doing
counts as reading. It is what we mean when we say something like "EQV is reading". To deny that you are reading this, here, now, would be to deny the whole practice that underpins the use of sentences like "EQV is reading here, now".
If we go back to the Trilemma, the leg we are on now is in effect that of circularity: we judge that you are reading because we judge that you are reading.
It might help at this stage to review the fact that a circular argument is perfectly valid, just potentially unsatisfactory. So it is not an objection to point out that the justification is circular.
And this is part of the appeal of
practice. The justification here is that this is
just how we use the words "EQV is reading" and their correlates. To deny that you are reading is just to step away from that practice. So someone who denies that you are reading isn't mistaken as to the facts, but as to the words we use to set them out.
And here we have avoided the picture of "conditions all the way down". Our justification is
this is just what we do.
Notice also that it's not some "fact of the matter" that settles the discussion. We've sidestepped that, too, by since we do not here point to a fact about the world, but to our practice within that world. In these sort of circumstances, we say things like "it is true that EQV is reading this post".
And we've dropped any need for splitting truth into absolute and relative truths. Our sentences are just true when the practice is coherent.
I'll stop there. That's enough for now.