Art is not a competition for "who can have the most humanity," nor "who can be the most 'gut-punchingly' truthful" (art is not truth). I grant that David Foster Wallace may have had great compassion and humanity within him; indeed, reading his work and essays, I'm almost sure of it. But art is also a creative act, a way of taking the everyday and expressing it in a manner that is heightened, of subverting cliches, of weaving things into interesting and unexpected patterns, of using the human need and capacity for storytelling to get something across. Wallace may have had great humanity, but when it comes to the basic fundaments of the art of writing - command of narrative, characterization, interesting imagery, lack of cliche, insight (he does have this occasionally rarely follows up on it), or even just the plain ability to craft an interesting sentence shorn of excess modifiers and - he is lacking. Broom of the System, for example, is a maybe interesting 20-30 page short story or novella, but he simply rambles on for far too long with nothing particularly interesting to fill up all of that space.
And I have nothing inherently against post-modernism, mind, but I think Wallace's particular brand of PoMo is of a rather lazy and banal variety.
Edit: but frankly, it's not a discussion that I care to have. If I'm right, time will do its work for me and bury the man's work. If I'm wrong, people will continue to be able to enjoy DFW to their heart's content. I frankly think that, even just a few decades later, the man's work is already quite dated and that it will only get more so as time passes. But, as I say, we shall see.