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Which island to pick for single male traveling alone for 3-4 months

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Trying to find information on a warm weather place to live in October through December. I prefer a place where I could find a cheap but livable apartment where I can relax but also enjoy a good nightlife. I have $7-8000 to spend and just want an extended vacation before I buckle down. Any ideas?
I keep asking questions in google and get similar answers all the time, including:
Aruba, Bonaire, jamaica, Dominica, Trinidad, Puerto Rico, Costa Rica and the Dominican Republic. The gran canaria was mentioned a lot too but I've been there before, along with Ibiza and Mallorca. Never been to the Caribbean though.
I know you can't predict what the weathers going to be like, but somewhere known to be more dry than wet is preferred. Also where the cost of living isn't crazy expensive. Like I said, I have about $7-8000 for airfare, a month-month apartment and everything else and I'm a single mid-20's male looking for a place to relax care-free and party with no responsibilities for a few months before I settle down. I just got out of the military and need this long vacation. Any advice would be appreciated. Thanks.

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