Colin, there are almost an infinite number of answers to your question...but very few that can be specifically useful. Here are my two, which are more general in nature:
1. The boat you ultimately select, because of your somewhat remote location and the limited inventory of boats in your price range, will depend much more on what''s available and much less on your preferred shopping list. IOW coincidence of what''s available in the marketplace when you''re looking will shape your choices moreso than is typical for buyers back in the U.S. Also, in the PR
locale where power boats are preferred by so many folks, you may well find the occasional small cruising sailboat that made its way to PR
from the U.S. to be preferred over the sailboats that are just used for daysails there.
2. Because of your limited budget, it will be very easy for you to buy too much boat and find the costs to repair what''s broken, service what works, and upgrade where needed (also don''t forget the cost of an acceptable berth) to exceed the funds which remain. This is turn may mean looking at smaller boats than you mention. A thorough, realisitic understanding of what work a prospective purchase will require of you in effort and expense will be critical to your choice. It is very, very common for newcomers to sailing with limited budgets to buy more boat than they can afford.
BTW I know of a completely rebuilt 28'' sloop with much cruising gear that is now being sold over in St. Thomas. Friends of ours moved up to a 43'' sloop to run a charter business and are looking for a buyer for the boat they sailed to Puerto Rico from Florida. If you''re interested in more info on this boat, please email me at the address below. The owners are very knowledgeable and I would expect the condition of the boat - mechanically - to be excellent, altho'' it probably lacks much cosmetic attention these days since they are busy with their charter business.