#1 for me. I've told him before that I'd love to watch him with someone else, that's the voyeur in me i suppose. I believe he'd get much enjoyment out of it if i were able to really get him into it, but till than I'll dream =)
As for a stripper, if I could get his hips moving right (no coordination) than I'd make him do it at my parties lol.
As a model, as Naughty Student said, "Love artistic nude photography". I'd be very comfortable with him doing that, he's always been the photographer, and never gets in front of the camera himself, and I think it'd help his confidence a lot. there are several guys that I know that want him, but he just shirks it off and calls it lies.
In the end of this weird post, I'd be comfortable with him doing a little of everything, I know that he'd always come back to me. I've pushed him past boundaries he never knew he had, been his rock, made him learn more about himself. I know I wouldn't lose him, but make his life more interesting.