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 waters.
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).