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Apropos of Nothing
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For a $2k boat that you don't intend on keeping for too long, I'd say you're putting too much thought into it. Just thumb through craigslist or that boat auction that RTB mentioned and pick something that looks not-too-bad.

At that price, the condition of the boat might dissuade your fiancee from sailing more than the boat's design.

That said, I've always liked the Flying Scots. You might be able to find one of those for 2k.

EDIT: You might also look into renting sailboats. You'd probably have a blast renting a pair of Sunfishes.
 
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