My brother lived down there and it was very expensive. He and his family rented a house, so he did not have to worry about buying one and then selling it before he went back to DTW. As far as bars, I could not tell you, as he is kind of past that phase. I can ask him some questions for you if you are really interested.
I flew cargo down there for a while. Cost of living would be quite expensive especially if you want to live by the beach. "The Jackalope" is a pretty fun bar that a lot of the pilots, at least the cargo ones, hang out at on Friday nights. Old San Juan is really neat to go drinking but if you're going at night have someone with you that knows the place well.
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