If I had my wish, I would buy one of the villas in Tierra del Sol, Aruba. Simply gorgeous, in the 250-500k range. All brand new, terrific desert landscaping, like living in an upscale Arizona community. Built around the golf course, each unit has its own pool in addition to a central pool/restaurant/spa facility which are all top notch. Diving on Aruba is good, weather very predictable, top-side features superb (tons of great restaurants, casinos, shopping, several golf courses, theaters, nightclubs, etc), currency is, for all practical purposes, the dollar. Traffic is much less than caymans, and no chance of hurricanes. Also, flights to Aruba are plentiful, the airport is good, customs are easy and quick and, best of all, you check through customs in Aruba, not the US. Thus, you don't have to waste time in international terminals in the US. And jumping to Bonaire is easy, where diving is better. Cost of living on Aruba is not exorbitant, and the breezes keep the bug population quite low by island standards.
Downside: Tierra del Sol has no beach access, but residents have free access to Palm beach through the Aruba Grand (but you have to drive). Also, if you don't golf, living on the golf course may not be a big plus. If you do golf, the course is wonderful, a Robert Trent Jones beauty that serves as a senior tour event.
I've stayed there and I've stayed in many resort condos/villas and this was the first facility that looked BETTER in real life than it does in its brochures or websites. Check them out, but leave one for me (if i could just convince my wife...)