hindsight2020

Caribbean-domiciled flying is generally low-hour low-pay work. Says here you're mil retired (assuming AF pilot) so you may not care about the pay differential.

Is the PR in your username stand for Puerto Rico? I'm a native and I can tell you there's nothing down there that would incentivize one to make it one's domicile (income tax being the big one) unless your immediate family has anchored ties to the island. My close family friend had a former Republic FO now working for him on contract basis (my friend has a part 91 management small company for non-pilot jet owners in Isla Grande). The cat was no kidding commuting SJU-IND for five years trying to make the family happy while trying to make a go at the airline thing, since the former presumably had no intention of moving to the CONUS, let alone the frigid Midwest, from the island. After 5 years he couldn't do it anymore and quit to fly locally for my friend in the island. I don't know what happened after that, it was 2 years ago since he told me this story.

I'm with you on the aversion to the cold. My wife has musings of living in the PNW after my mil retirement. Hope she doesn't divorce me over it because that's not happening LOL. I think we're gonna end up doing a lot of snowbirding after I retire from the military and I go dabble on the airline thing. I'd love to move back to PR and do milk runs around the Caribe year round, but I can't afford it. I certainly don't want to lose in-state residency for my son when it comes to college. After all, that was the whole premise of me leaving the island post high school.

At any rate, in your case I think Florida domicile and pick a regional with heavy caribbean footprint, and bid aggressively to stay in the southern side of the city pairings. Good luck. At least you got the check of the month club, I wish I was there myself already (7 effing years to go....)