Is Steve Catholic, though? Otherwise I think the 20th-century changes in Catholicism would interest him (if only because I find them rivetingly interesting myself, as a historian who studies the 20th century in a very Catholic part of the world) but they might not be instantly obvious to him.

There's some discussion of how New York has and has not changed in the follow-up post to this one - I agreed with you, but idlerat took issue with me and she may well be right. So you might want to look at that. I do like your point about the "uncanny valley" though - that's a great observation.