Not really a suggestion, but I've met some couples that have done that in Grand Cayman. One such, though not divers, are Canadian, and had to relinquish 100% of everything Canadian except their passports.
No matter where you go - I'd suggest taking over an existing business - that a local has setup and is for sale - that is convenient for you. Makes immigration much easier. The usual "route" is motel/hotel/resort.
Then if you get hit by a hurricane & lose everything, well, that's life in the tropics. A guy I know that was doing IT work & living in BVI finally came back to Canada after two hurricanes & countless storms.
Robert Palmer famously "left" the Bahamas because it was at the time (mid-90's) according to him being overrun by gangs & drugs.
Ask Quero - she went the opposite way to Thailand. Another Canadian from Montreal is planning on leaving everything behind and setting up shop in that area too. Cheap cost of living, excellent diving.
If you were American, I'd suggest either somewhere in Hawaii or Puerto Rico. As a Canadian - scratch anything US-based - unless you immigrate as an investor-business.
Interesting thread for sure, looking forward to comments.