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One thing to add to this discussion— DFW's description of the Federer/Agassi point in Roger Federer as Religious Experience doesn't actually match up all that well with what actually happened.

See for yourself: https://www.youtube.com/watch?v=jDwG5rJVtdc

And note the discussion in the comments about the video not matching up at all with DFW's description, despite key indicators that it is the point DFW was talking about[1].

[1] Key indicators such as Federer's backsteps and McEnroe's commentary.

Though I have a great appreciation for DFW's work (the linked article even links to the early essay of his I resurrected from paper), I found he tended to exaggerate, at least when discussing topics I'm knowledgeable about. (In particular I'm thinking about some of the math in IJ, but I know I have this impression from more than just that.)
I'd like to point out the following paragraph as evidence of a rather hackerly trait in DFW.

"The publication limited him to 1,000 words, which Wallace elided by transgressing the traditional review format. He composed the entire piece as a series of bullet points, each beginning with a dependent clause followed by a colon (which functions as a verb)[ix] and then a predicate. His rhetorical reasoning was both innovative and ironic: “Tactical reason for review form: The words preceding each item’s colon technically constitute neither subjective complement nor appositive nor really any recognized grammatical unit at all; hence none of these antecolonic words should count against R.T.’s rigid 1000-word limit.” He called this 'new, transgeneric critical form: the Indexical Book Review.' "

I've always thought of a lot of DFW's writing as a kind of programming. There's the main narrative thread of whatever he's talking about at a given time-slice, then there are the "worker threads" he spins off from that in the form of random lateral jumps to stream-of-consciousness, the 24-page footnote containing a single run-on sentence, etc. Certainly in IJ, and to a lesser degree in his other works, there are multiple "paths" the thread of execution can take to reach the end of the book. Put another way: are DFW's footnotes intended to be read synchronously or asynchronously? If you read them synchronously, it tends to interrupt the flow of the main narrative (context switches are expensive). If you read them asynchronously, you miss a lot of context and, possibly, the author's intended ordering/synchronization of the ideas. And of course all of this is intentional, and gives his writing a "meta" dimension that standard English don't usually have (usually for good reasons).
Has anyone who possesses the requisite math background read DFW's "Everything and More: A Compact History of Infinity"?

When I read it I wasn't equipped with the math to understand the more technical parts, yet I still enjoyed it. Perhaps I was naive though, and to the intended audience it doesn't hold up for one reason or another...?

Two David Foster Wallace posts in two days, I can't complain about that.