Really interesting stuff.
I really like Henry James, and following on from your stuff about the Eton teacher/ J.Peterson fan last week, I think you'd enjoy his novel "The Bostonians", about the complicated relationship between a charismatic feminist speaker, (whose speaking engagements make her resemble a public intellectual from our time) and a reactionary Southerner. I wrote about it before here:
https://www.cookdandbombd.co.uk/forums/index.php/topic,62777.msg3523276.html#msg3523276I think your point about his work taking place in a very privileged world is a fair one, but I would say that he uses it well- for example, the plot of his excellent, well-crafted and mysterious short story "The Pattern in the Carpet" could really only have taken place within the comfortable world of literary criticism.
I have a lot of sympathy for people who are suspicious about just how much of the literary canon involves the lives of the wealthy, but as with George Eliot and Thomas Mann, the pleasure in James' best bits is the pleasure of thinking about the dilemmas that would face us even if out material problems were solved. As for the example you pick- well surely marrying the wrong person is one of the worst mistakes a person can possibly make, regardless of their social class.
His later books like The Ambassadors are really difficult to read, but I did get the sense, as I struggled through that one, that he was trying to show something about the way the culture around him was starting to decay a bit, and that the main character Strether's weakness and indecisiveness was mirrored in the torturous sentence structure- but maybe the book is a much a symptom as it is a diagnosis of the problems he was talking about it.
I also went through a Burroughs phase when I was younger, which I'm not particularly embarrassed by. "Naked Lunch" is inessential, and not to be taken seriously as a novel at all, but it is funny- it always struck me a being a really horrible cousin of the Monty Python TV series. The freeform nature does not come from a pretentious/pseudy/arty attempt to transcend regular literary forms, I just think he had no idea how to write a novel and so put together a bunch of amusing/disturbing sketches and was lucky to find an audience with it.
"Junky" is very good at introducing the reader to the weird language and ritual of the mid-century US smackhead sub-culture- and a lot of the phrases from it. have stuck in my head for years.
I'm down to my cottons, so I've got to get a croaker to write me a script for some yellow jerseys, or I'll have to go out lush-working again.etc. I don't know if it's realistic, mind you, but I can't fault it as world-building.
Your moral condemnation of his lifestyle is totally appropriate, but I doubt there was anything pseudy or pretentious going on there, if anything I suspect he was stunted and adolescent in his worldview.
I had almost exactly the same reaction to the Camus novel as you did, but I suspect that his motivations were genuine in writing it- my guess is that the world Camus was raised in was much, much more conformist than the world we live in now, and what seem very sensible and appropriate conventions to us may have seemed arbitary to him because there was more of them.