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Old 11-29-2012
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Re: Beginners Boat

A keelboat is [generally] more forgiving, a centerboarder is [generally] easier to trailer.

A $1k-$2k budget has you in the category of small day sailor (or larger fixer-upper). Some examples that might fit the bill:
laser, capri 14, hobie 14, precision 15, amf puffer, sunfish, muntineer, and a whole slew of other small trailerables.

Craigslist is your friend... and if your only spending $1-2k on a sailboat, expect to put some more money into it for "upgrades" in the coming year. Including the biggies that everyone forgets to include in incidentals, like life-jackets!

At that price range you'll also have to become your own boat inspector... anything with a trailer will also require you to become a trailer inspector... look for dry rotted tires, and non-working lights... and expect to have to fix both.
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