A used sailboat can either be an incredible bargain or a colossal wallet-drainer. Much depends on how sharp as well as informed you are during the buying process.
General
Take an expert with you. Some of the faults of a sailboat can look awful but are easy to repair while other faults are hidden as well as expensive. For a beginner, it's really hard to spot the difference. If you don't have a friend familiar with boats, consider hiring a professional. It will be money well-spent, especially if the boat is an expensive one.
When bargaining, make a list of stuff that needs attention as well as refer to it when you make an offer. When sailboat owners sell, they've either got the hots for a bigger boat or they're getting out of sailing for good. In either case, they're motivated- so don't be afraid to lowball. If need be, walk away. Chances are you'll get a call the next morning.
Find a reliable mover/transporter to transport your sailboat. There are hundreds of feedback-rated sailboat transporters on www.uShip.com.
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Added: Thu Feb 02 2006