I just went through the same thing
Hey Mike,I just bought a boat in Mystic, CT--not too far from you. Mine is a 1977 that had tired but intact sails, Loran, depth, a ragged dodger, wheel steering, a totally blown motor and a good, clean interior. I picked mine up for $10k. After getting to know the boat for the last 4 months there are a couple of things I'd look for:1. Starboard side chainplates & where stress would channel to the hull. The starboard side on these boats is a little weaker than the port, due to less bulkhead area on that side. Check under the seats to see if the fiberglass is showing signs of stress.2. Check where the mast is stepped - both inside & out for signs of crazing or cracking.3. Check the deck for crazing around the railings.Overall, I found that I needed to invest about $22k for me to get a boat that was perfect for me: a new genoa, new engine & a few odds & ends that were important to me. My philosophy is that I can spend about 15 to 20% over book value, including ALL improvements, for a boat that I'm going to keep for 4 to 5 years. That way I'll get a chance to use an ideal boat, get my money's worth & not take too much of a hit when it comes time to trade up.If you use a formula like that it's surprising how easy these financial decisions can be. It sounds like you've got some $$$ you're going to need to put into her. As you probably know, a sail, a dodger, some electronics and a few odds and ends can quickly add up to over $3,000. Overall I am completely thrilled with the purchase of my boat, but that's because I knew how much all of my improvements would cost. Be sure you add everything up & check your total investment against the BUC book.