Looking at a free sailboat, what could go wrong...

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Still waiting for a response from the seller, but looks like was registered last year. Thinks it's the 20
 
@pooriggy - is something like this usable in the shallow bays ?
@pooriggy pretty sure it's the 20, as it only has one window, been reading lots on sites like this but not sure why boat was only made for a few years. https://forums.sailboatowners.com/threads/oday-20.175514/.

Pat, it's a centerboard, which is why I'm interested. Can trailer to boat ramps and keep in the garage. Though gotta see if my new hitch can tow that weight
 
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What should I be looking for?
'73 O'day
Learned to sail on an o'day on LI and ended up racing at raritan yacht club, but haven't sailed in a long time. I guess if i was about to take someone's money pit: Is the seller willing to put the boat in the water and take it out for a sail, show you how it handles and how she sails. When out on the water, is the deck flexing as you move around or when you use the winches. How much water accumulates in the bilge, can the bilge pump keep up. Look out for soft spots in the fiberglass, especially the fiberglass around anything mounted to the deck or penetrations through the deck. Any soft spots or movement in the fiberglass is water damage and will need to be repaired. Are all the mechanicals operational and smooth to operate, or is that another expense? Electronics operational? Teak rotted out? Cracks in the underside especially around the rudder mount points and the keel. If serious, a qualified marine surveyor will probably cost around $1k, and then you can start to Bill On Another Thousand. Or charter a moorings boat in the BVI for week.
 
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