It is about personal preferences. For me:
- Bonaire - lack of crowds, ability to dive 24/7, being able to set up/break down my own gear. I like that most buildings are 2-3 stories max. The first 4-5 years I thought the Dutch rather aloof as well, until we got to know a bunch better and I think established our street cred. Now we exchange cards, emails and travel updates throughout the year. Bonaire is a DIVE vacation, a bunch of other places I've been have been vacations, with diving.
- Saba - also a dive destination, but talk about remote, the diving is mostly deep, all boat, really limited lodging food choices and far easier to be blown out. Crime almost non-existant, people lave thir doors unlocked.
- St. Martin is a beach lovers dream, gastronomic delight, shopping mecca (jewelry!!!!) The diving is better than advertised, again boat. Parts of the island are a bit sketchy, I wouldn't drive through after dark.
- St. Thomas - easy to get to, crowded, nice diving. Good food, good shopping.
- Grand Cayman - my second favorite island. Easy to get to, increasing amount of shore diving (swim out distance varies), deep dives on North Wall, great fun shallow dives off 7 Mile Beach, beautiful island, fantastic food, big stuff, small stuff, activites to entertain non-divers, wonderful people. I feel almost guilty having people setup my gear, switch tanks, break gear down, not sure why. At the end of the day, much of GC seems like another over built commercialized version of the US and very expensive. Now if someone gave me a condo or townhouse and I had to move there, I'd be thrilled!
- Bahamas - haven't seen enough as a diver to form a real opinion or done the smaller/outer islands.
I would certainly go back to any of them, just let me grab my passport.

Right now looking to do some reading on Bermuda for a long weekend and add another island to the list.