As someone with no plans to live or vacation in the caribbean, I'm curious. Is there a specific notable reason, or is it just a combination of littler things (cost, convenience, politics, weather, etc.)?

I've spend a total of about 2 months in the Carribean. One of those being an entire month straight.

It's the convenience really, and the fact that nobody is in a hurry. Island time is real. You cannot be demanding. You can't really be upset at service. Most people are there to chill out, even if they are doing a job. Life is just slower.

This is good, IMO. But if you are a hedonically adapted/burned out western metropolis dweller, this culture shock could be distressing.