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I agree with the idea that there are bargains Stateside, but you should also look at Panama and Trinidad. Many an optimistic voyage has started with a great, well-equipped boat and a poorly equipped marriage: you can get "priced to sell" boats in good shape except for the bird **** on the decks if you budget for flying in yourself and a surveyor for a week for several boat visits.
Which boat you buy depends on how "shore-independent" you wish to be, and whether you intend to dawdle or to go point-to-point as efficiently as possible (the difference might be two knots of speed, mind you!).
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