If anime taught me anything It's that character development is just padding

The Road is one of my favorite pieces of writing. It's art like anything else. The lack of punctuation really made it feel raw and close to home.

I agree. I read The Road recently since it's my wife's favorite book and holy shit it was exhausting at times. I enjoyed the story to a degree, but the stream-of-thought writing style and unspecific grammar took me out of it. If it had been written in a more understandable prose I think I would have enjoyed it more; but would it have been as famous then I wonder

If you were to take the list of all professional basketball players, and sort them by the number of free throws missed per game, you'd see the top of the list is dominated by Hall of famers.

That's not because missing free throws makes for a good basketball player. Or even that it isn't important in basketball to be able to make free throws. It still remains important at every level of the game! But some of the people who miss a lot of free throws were just so utterly dominant at other parts of the game that they had long successful basketball careers despite being bad at an important skill for basketball players.

Cormac McCarthy and James Joyce have a signature style, yes, but I'd argue that they're successful despite that, rather than because of that.

Joyce is meant to be read like poetry. It plays off the sound of the language. His stuff is genuinely awful to sit down and read, just like it would be awful to sit down and read through a collection of poetry (to me anyway). Some Authors play with language in a good way, like the way Hemingway rarely attributes dialogue and forces you to pay attention and understand why the character would say something like that. It also reads very minimalist and leaves a lot to your own imagination and voice.

I think you're in the vast majority.

When it comes to the readers expectation, things become a lot more complex. I don't remember the exact words, but Brandon Sanderson talked about promises to the reader, where it's OK to do surprising things, but expectations must be carefully managed in that surprises must not feel like betrayal. Poor execution of this is why everyone hates the "...but it was all a dream" trope.

Ok theres 2 replies about Cormac McCarthy, there's clearly something I'm missing contextwise about understanding rules and how to break them.

This is not an inflammatory response, I am just curious- How do you feel about "House of Leaves?"

Generally considered to be a phenomenal work of art, but it DEFINITELY doesn't follow the vast majority of standard grammar rules.