"the real question is "
And the answer is, if it was that simple you'd find people already doing this WHOLESALE.
Among other things, you can't buy and sell sailboats like shoes. You are looking at buying
, selling, and IMPORTING titled property across international borders. There are all sorts of issues with ensuring that you have good title, changing the vessel's flag (and title) when you bring it across a border, potential legal
problems, questions about tax and duties.
And then, you're still dealing with sailboats that can take 6-12 months to sell once you bring them back, even at "the right" price
Traditionally the best place to buy a sailboat is supposed to be at a major "downwind" destination
, when people realize they're going to have to beat upwind a thousand miles all the way home, and they put the boat up for sale
and fly back instead. But all that can get swamped by the question of whether any particular boat is a bargain--or not. And the expenses of going wherever you plan to buy the boat--and then doing local surverys, etc., and hoping you can pick one up that meets your needs. Without having to use a foreign legal
system to iron out any problems you may later discover with it--like liens against the boat.