Ok I'll bite
First don't buy anything with big holes in the hull. Sorry I couldn't help it. BUT SERIOUSLY, if its out fot he water you like to tap around on the hull to look for soft spots and blistering of the paint. Also want to see the leading edge of the centerboard housing or keel, How banged up is it? It that area sound? Then you want to get on the topside and look for patches or soft spots (repair of old soft spots) are the stanchions all tight so they move so that water could get under them and into the core. Looking inside for signs of water stains (from leaks) check the sails for wear or staining. Is the transom solid? Is the mast step (the place where the mast attaches to the deck) solid does it feel spongey? From the inside can you look at the seam between the deck and hull and see daylight. If the rigging, hull and deck are solid and there are sails then you probably have a boat that will sail. So then its a matter of how much you pay to own it and/or can you do or pay for the fixes if needed. Good luck,Mike