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I second SPI or Hatteras. Wind not 100% guaranteed but everything else on your list is, plus SPI is cheap and fairly easily accessible. Fly into Harlingen, Brownsville, or (a little further) McAllen. Nightlife is kinda lame but you also have to know where to look. Haven't been to Hatteras for ages but went when I lived in Boston, and October is typically windy there, but not always beginner-friendly wind. Water is shallow and warm in the bay. Save the more exotic trips for when you have time (and skills) to explore.