I think I would go for either Bandon, or somewhere in Ireland. Almost every caddy, I have had in Ireland added a lot to the day, they were funny, made fun of you and had a great time. If it were me, I would not want to caddy at a private club where members and their guests expected a buttoned down "yes sir" type of experience.
I figure if you are not going to go overseas, you could probably get away with that at Bandon.