I tried to read it. Really, really tried. For my head it's utterly unreadable. Had to give up after ~30 pages.
The writing flow and style of that book can be best described as "long-winded, over-extended, bloated and bloviating, rejected entry to Bulwer-Lytton contest".
I also like writing that is clean, pure, poetic and emotionally authentic. I feel like some of those authors (I'm looking at you, Wallace) are outsiders sniping at mainstream culture with hipster snobbishness. I used to sorta be that way, but I can't relate to that anymore.
I think folks like Martin Amis did it a lot more entertainingly, though the self-aware sophistication is (sigh) a lot to bear.
Where DFW embodies the virtues you admire is his non-fiction -- Consider the Lobster and A Supposedly Fun Thing I think are fascinating expositions into just how far down you have to dig to get at the emotionally authentic.
As for his fiction, I don't think he lived long enough to get all his sophomoric ideas out and get to material that actually mattered to him.
I didn’t find Infinite Jest nearly as difficult.
This is how I felt about his cruise ship manifesto. I get it, I get it, cruises are lowbrow, tacky and suck. But spare us all your hipster cooler than thou angst.
Before giving up I'm going to try to read one of those book summaries or an analysis to try to regain my footing.
Whether it was worth the time invested is another question entirely. ("No", I'm afraid, is the answer. There are better books along the same lines that are also challenging but less so. I recommend 100 Years of Solitude, Midnight's Children, or Tin Drum).
Avoid Ulysses. There's such bad, lame "philosophy of math" in there it really turned me off, made it seem like the whole book is just Joyce showing off how smart he thinks he is.
That book sat on my bedside table for months, making me feel bad for being unable to finish it, and giving me absolutly zero joy while I was reading it.