That's an interesting take on Wallace. Again, going back to D.T Max, he was asked at one point, I think it was in an interview, about one scene in Wallace's article on the cruise ship. Wallace was looking at the ocean and he was saying that the ocean was vast, dark and empty. Don't quote me strictly on that. But I believe he said something to that effect.
Max asks, was that Wallace simply describing what the ocean felt like to him or was that his depression talking? I don't know. What you say about Wallace constantly tormenting himself reminds me of that.
And I think this is true. It's hard to explain Wallace better than he explains himself, but I think one can say that his acute and amazing powers of observation and detail must have applied to everything, not only his short stories or his books, but to himself too. It's the price he had to pay for the gift he had.
Nevertheless, I still think sincerity is sincerity and that can be used in a perverse manner too. But by now, given how much literature has expanded, it's just extremely hard to come up with something new to say something tried and true in an original manner. So it's said "naively" as it were, and can come off as cliched. Too bad, but, then again, this is person-dependant. What I find to be just cheesy sentimentalism, others find profound. And what I find deep others find verbose or obscurantist. Oh well.
I got to page 450 of Infinite Jest and just lost interest. It did not grip me like his other stuff. And I do believe Gravity's Rainbow and Mason & Dixon by Pynchon to be quite harder to read than IJ. It's just a matter of taste. I loved his other stuff, not his novel. The endnotes did it for me, it made reading way too slow.
On the other hand, these very same techniques in his essays and short stories are a true pleasure. And some will like all of it some parts of it and some don't like Wallace. Just like some hate Pynchon. It's all fair.
What I do think is that Wallace was unique in being able to express himself with such precision that is almost unmatched. He could easily form sentences and paragraphs around ideas that would take other writers entire books to try and elucidate.
I think his critique of pomo in literature is completely legitimate. And a serious problem for writers thinking about creating a "new style" or genre. But in real life you can get stuck in the images and the "narratives" while setting aside power structures. In a way, it's like wrestling with authority on authority's terms. So you can take the Iraq war and just treat it like a TV spectacle and you analyze that. But then you don't mention the millions of civilians which were killed. And that's a problem, if this is overlooked.
Not saying it to you specifically, just speaking in general terms.
Having said this, he could very much describe the "water", which we take for granted, such as being in a luxury cruise and being amazed at how comfortable he was in his room, with all the luxuries given but then describing how in like a day or two, he was upset his waiter brought his room service 10 minutes late. Or him pointing out that we take a sunny day as any other, don't even bother to think about it. But if we knew it was our last day on Earth, how much we would appreciate every little detail.
In the end, it really is about being aware. Which is easy to say and so hard to do all the time.