Your thoughts on Albergs and Islanders appreciated
I''m a bit less dubious of Plan A than Jeff, as trade between Cuba and 99% of the world is relatively straightforward and corruption when bringing things in from outside that island nation appears to be less than many other ''3rd world'' countries. But doing a refurb in Cuba would definitely be a huge hassle, especially when folding in the everpresent officaldom that must be accommodated at every turn. Why would you put yourself in that position? Good (some great) craftsmen are in other parts of the Caribbean. I would caution you in accepting yor friend''s assurance that "the project is possible" when his reference point is a home and yours will be a sailboat.
OTOH your notion of improving the boat *after* the cruise begins can lead you to a pretty creative, satisfying agenda of ''restoration steps''. Friends had their Perkins totally rebuilt while in Luperon, DR by an authorized Perkins dealer, all legitimate Perkins parts and a full internal rebuild, for $3K - and that included the dealer pulling the engine and trucking it across the island to outside Santo Domingo plus reinstalling it. Was it done to ABYC standards? Did the joinerwork in the boat escape any nicks & scratches. Well, every bargain has its compromises. Both Trinidad and Guatemala are known worldwide for their hardwood forests, and wood craftsmen are easy to find (tho'' they may know nothing about boats, which means you need to know what you want and provide constant supervision). Stepping outside the most commercially developed countries means being outside a company''s distribution network, so you can negotiate a large purchase directly with the manufacturer at a savings - e.g., a fellow I know ordered a new Westerbeke diesel directly from them while in Trinidad and did a total install, soup to nuts, for 2/3 the cost - in part because of the reasonable labor rates, as well. So...as you can see, lots of ways to accomplish what''s important to you. But as I struggle through a fairly extensive refit before more extended cruising, running one day to the metal shop and the next to a marine electric shop, the thought of doing it in a resource-limited locale makes me shudder.
Feel free to shoot me a question anytime you think it might help; and good luck on The Search!