Since you are working in the summer, my vote would be for the Gulf. Lots of choices for the winter - Keys, Bahamas, Caribbean.
At your size and price range, you are looking at a project boat. Expect to put a lot of time and money into it before its ready for a "blue water" passage.
Yeah, it certainly seems to make more sense. I guess my main reservation is the desire to eventually sail the Pacific, but that is a couple years out still, so I shouldn't let that dominate this more immediate decision. Plenty of time to get over there, I suppose.
And yeah, I'm planning on putting a year's worth of time and some money on fixing up whatever I end up with. Although, not to sound too naive, I'm getting the impressing that if I wait for the right deal, $15,000 has a chance of getting me something that isn't going to require massive, fundamental modifications to be that seaworthy, especially in the shorter length boats. I'm definitely willing to sacrifice comfort and aesthetics for a solid little boat.