I was looking for some insight into working in the Caribbean. I've spent a lot of time lately contemplating different options to leave Canada and move abroad. I'm looking to go somewhere I can fly with my Canadian license, as well as "never see snow again" (Thank you Nunavut. You ruined it for me

I searched for a list of potential airlines I thought might hire Canadians, but I must admit I have no idea what type of requirements they have. I'm willing to fly anything, as long as it's stable and offers a reasonable salary / standard of living. Most of my experience is on turboprops (medevac / regional) but I also have some jet time, 1400+ hrs or so on corporate and regional jets.
Some of the airlines I looked at:
- Cayman Airways (Cayman Islands - Twin Otters, S340, B737Max)
- Inter Carribean (Turks & Caicos / Barbados, E145, ATR42, E120)
- Winair
- Aruba Airlines
I'm also open to fly corporate.
Have any of you flown there? How were the working conditions? What about lifestyle there? Was the cost of living expensive?