I am a bit surprised by your and angusiguess's take-aways from DFW. For me, the technical details of IJ were absolutely uncritical parts of the story - I imagine that the setting could be changed if DFW wanted to. Much more interesting for me was the absurdity of the characters, the physical pain and nausea caused by reading the book, the mental strain, and the story itself. The most memorable things about IJ are the effects that reading the material had on me, not so much the contents of the material itself.
If anybody has not read What Happens at the End of Infinite Jest [1] by Aaron Swartz, you must.
I don't know how it ends and I can't read the end. Every time I try, I have this strange feeling that as long as I don't read it, it can't happen; what ever it is; that the story, and the fate of all those strange and magical personalities hangs in limbo until I - specifically, I - finish reading, at which point the whole house of cards will simply spontaneously combust and leave me with a pile of ashes in my lap and smoke in my hair. I've never been involved with a book like IJ before.
The fate of all those strange and magical personalities hangs in limbo whether you stop reading close to the end or at the actual end. The last scene reveals one piece of the puzzle but it doesn't really conclude the story.
I should clarify that I don't see technological implications as central themes in IJ, but I do find it really intriguing that rather than excluding or hand-waving issues that have to do with technology he dives in and gives them what seems to me a great deal of good, hard thought.
The book hit me really hard emotionally as well, and for me a lot of the anxiety centered around how fragile our assumptions are with regards to communication. All of DFW's exhibits to me a neurotic fixation with the other person understanding exactly what you mean (compact history of Infinity especially, where the book reads differently depending on how comfortable you are with exploring some of the proofs and concepts involved, you could skip the I.Y.I's and still get a really strong and interesting book, but the experience would be different), and it is a lot of that anxiety that hit me hard.
It just seemed interesting to me that technology and media fit so well with that central emotional point. If we can't even communicate to people in writing or speech, mass communication could fare not better.
It's sort of like talking about all of the AA reference in the book. As a topic there are a lot of things you can say about addiction and rationalization and human ritual, but AA was just a handy analogy to talk about all of that stuff, and more importantly to evoke certain feelings in the reader.
It's easier to talk about the set pieces of the book than it is to try and clearly articulate how it makes me feel, is all.
I don't think DFW set out purposefully to write a technically accurate prophetic piece of science-fiction in the way Clark or Asimov did, he wrote out of the typical literary author's urge to clear away an individual's crushing existential dread.
What's amazing is technology in American(or O.N.A.N) culture is presented as the cure for existential dread, so the technology itself is a like a literary character, it's almost the antagonist.
If anybody has not read What Happens at the End of Infinite Jest [1] by Aaron Swartz, you must.
[1]: http://www.aaronsw.com/weblog/ijend