I'd recommend seeing if you could sign on as crew on a delivery
for someone else's boat first. You'd learn from the captain
& you'd have that additional experience to add to your sailing resume. Plus you'd get to find out if you really enjoyed the experience before taking the leap.
We write Marine Insurance with about 30 reputable insurance companies.
Only 4 of them write full time
coverage in the Caribbean
1 of them requires 3 years experience with a similar boat.
1 of them won't insure a boat that's valued at under $500,000.
1 of them won't insure Americans in US or Caribbean
So you see that only leaves you with a small number of reputable companies (1 or 2?) to choose from.
If you're willing to be a snowbird
- dip into the Caribbean during the winter and then sail north of the hurricane
box in the summer - there are more companies to choose from. You'd have to get north of Savannah, Cape Hatteras or similar location during hurricane
season (approximately June 1 to Nov 1).