Wow, thanks for all the quick replies!
I know it's going to be a stretch finding the right boat. I won't have so much cash until I get rid of this powerboat of mine, and I probably won't be able to do that until the weather breaks and I can put it back in the water.
I really don't mind cleaning boats; doing upholstery is a little more advanced but probably nothing I can't tackle (I redid cushions before, but they weren't the kind of quality you'd want to sleep on). Is there a good checklist out there that I can take with me to try to sniff out defects and maintenance areas? Clearly it's not too hard to determine whether a sail is shot or not but there are a lot of subtle things that I probably will miss unless we rig up the boat there on the spot.