I went to Puerto Rico last winter for two weeks last February and it was the best. I stayed in San Juan and met up with a local skate rat who had pretty extensive knowledge of the whole island. The locals said the water was cold, but it was actually like bath water. I thought for sure my friends and I would have a tough time with spots but there was actually a lot of plazas that were mostly smooth and equipped with some kind of marble or granite. You'll run into rugged shit for sure, but it was one of the most productive skate trips I've been on. The food wasn't anything to write home about, a lot of chains and the stuff that was independent was usually kind of bad. Beautiful weather in February, beautiful women, great coffee. Old San Juan is definitely the tourist area but visually and party wise would probably be the most pleasant to stay in. We stayed at the San Juan International hostel and while it was cheap, it was a little disconnected from the night life and was in a sketchy area of San Juan but we didn't get fucked with by anyone in the area or at all on our trip. Local skaters were cool as shit and I would recommend renting a car, public transit isn't good there.
Is that enough convincing?