I would heartily recommend DFW, and only with a few small reservations. He's stimulating and expressive and inventive with the English language. He's really smart, and he knows it. Sometimes this self-possession leaks into his writing and this rubs some people the wrong way (an example would be his tendency for verbose language where simpler may do, but to me this is a matter of style). But at the same time, he was incredibly hard on himself. He cherished the general reader, striving to respect her intelligence. Some of his writing is the most expressive I've ever read, nailing down thoughts, associations, and feelings that I chalked up as non-communicable, or that would otherwise require some sort of brain interface technology because those thoughts operate at a level beyond words or even pictures.
I roughly recall that KB thinks DFW dazzles with words rather than true insight. But I find DFW an enormous pleasure. He's at times irreverent then sincere, a-million-miles-a-minute and then slow and purposeful. I've never had to use a dictionary more than with Wallace. Or temporarily stop reading just so I could enjoy the sheer power of what I read.
For his fiction, my favorite short story of his Good Old Neon.
Edit to add: the original essay I linked, called Authority and American Usage, ranges all over everything you guys touched on in this thread. I can't imagine a more relevant essay, and from one of my favorite authors, so I felt very compelled to recommend it.