You use encryption every day already, you just don't think about it.
For all of HTTPS's faults, it's so transparent that you don't even think of it as encrypted communication. If PKI apps and MUAs didn't suck so much, we'd probably all treat email the same way.
I would definitely use HTTPS, but that's not really what I had in mind. When I said I wouldn't use encryption I was thinking specifically about PKI stuff like PGP, precisely because like you say, it sucks to use it. Badly enough that I think it would make you stick out and receive additional scrutiny if you did.
For all of HTTPS's faults, it's so transparent that you don't even think of it as encrypted communication. If PKI apps and MUAs didn't suck so much, we'd probably all treat email the same way.