Join Date: Oct 2009
Location: Gloucester, MA
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The best thing that you could do would be to talk the owner into a test sail along with a visual inspection. During the test sail, watch everything that is done, see whether it makes sense and try everything you feel comfortable doing. Unless the boat has been significantly modified, it was a relatively good design to start with.
In your inspection, really take your time and go over every inch of the boat. Some areas to pay particular attention to would be the condition of the rigging, sails, centerboard and pin, chainplates, and rudder. Bring a digital camera so that you can show the pictures to others and they can help. Depending on how you work, this process could take a few hours to go over the boat. Don't be afraid of crawling into every place accessible with a flashlight.