Probably one of the most unlikely guys to talk about some of the interesting/terrifying implications of technology on communication and interaction (among many other things)
I wouldn't necessarily call him "unlikely" to discuss those topics. While he wasn't a technologist, per se, he was certainly more inclined in that direction than most literary writers of his generation were.
In fact, he wrote an entire book on the history of transfinite set theory. (From a layman's perspective, sure, but how many other non-sci-fi writers claim to have such interests?)
For anyone unfamiliar with his work, I can't recommend him highly enough. Especially to the HN crowd. He's very discursive, and he rewards long attention spans. But he's worth it.
A Compact History of Infinity was pretty tremendous. And while it makes some amount of sense that he's be apt to deal with questions of metaphysics from a formal standpoint, there are some more unusual topics in there, like that bit from Infinite Jest about the evolution of videophones and the use of masks.
I think some of his best work centers on the ability (or even possibility) to communicate with other people, and how technology has a lot of potential to disrupt it.
