Never been to Chicago, so I doubt we'd meet.
If I did live in Chicago, know Harry, and know what we all know about him, I'd move. Also given what I know about Chicago, I'd probably want to move anyway.
I'm pretty sure Harry comes across as "off" to most people most of the time. The rest of the time, he probably comes off as terrifying. I've had plenty of friends in the first category, and Harry seems like the kind of off I'd get along with.
The problem with Harry is he's probably the kind of guy who it's hard to be friends with. No cell phone, erratic work schedule, unreliable car, no electronic communications. I'm friends with a guy like that, but I'm not sure I'd maintain the friendship if I didn't work next door to him because I'd be the one maintaining the friendship, not him.