We did what you write of doing...bought a boat in the Islands, one hurricane season in Grenada
and Trinidad and three in the ABC's...sailing back to the US just before hurricane season is just hard work
. That plan allows you to get experience without the hard work and risk of 'getting down island.'
You should develop criteria for your 'ideal' boat and start looking in the US but if the ideal boat is in the islands, like our's was, then buy in the islands.
Getting down island from the Chesapeake is not a benign proposition, two of the most experienced circumnavigators I know argue strongly against the trip. I have done the trip 5 times, however, 4 of the 5 trips were from much further south than the Chesapeake and in the Spring having wintered in Florida
and the Bahamas. The trip is based on the false proposition that
'there is a weather
window between the last TS and the first winter storm on or about the 1st of November.'
Several boats and at least one life have been lost
in early winter storms and it is only a matter of time before a TS/ hurricane catches the fleet off-shore.
The 'Thornless path' of Van Sant was just too much windward work, the off-shore route
is much easier providing you start south of Hatteras. More motoring but less chance of getting caught by a winter storm in the Gulf Stream
Enjoy, we spent 6 years in the Caribbean
and loved every minute.