The Turks & Caicos and
Belize seem to be the place Canadians go to, I assume the immigration issue has something to do with it. If you've got money, it's not too hard to get the right to reside on the Bahamas. Working there is a different issue though. Basically if you buy a house worth at least US$250,000 you automatically get the right to reside, and if it's worth $500,000 or more you can eventually get permanent residency.
Some political party on the Turks & Caicos were campaigning for the islands to become a Canadian territory instead of a
UK one some years ago, because Canada is closer.
I think Trinidad & Tobago and possibly Barbados might have similar rules to the Bahamas, I had a friend who lived on Barbados and he didn't have any immigration problems, but he was loaded.
Yeah, if you have a claim to citizenship in an EU country that would help with St Maarten and Curacao as they are both territories of EU States. St Maarten is a French dept. so that would probably be the easiest. I heard the
Netherlands had tightened rules on vacation homes for retirees so there is a lot of cheap property going on Curacao at the moment.
Remember the tax rules though, French tax laws are appalling and the Netherlands aren't much better.
Steve.