I would have no problem buying a boat with a hole in it. But that isn't to say I would even take a free boat with a hole. Depending on the extent of the
repairs, and the other things wrong with it, while it may be possible to fix a boat from any condition, that doesn't mean it is economical to do so.
For instance, post Katrina my uncles Trip 40 was found in the parking lot of our yacht club. The boat was literly in three pieces, the keel snapped off, the transom was crushed by a tree, and the mast was wrapped around a light pole. This is all reparable damage, but a good used trip was $40,000 and the
repair bill would have been more than a new one.
My fathers boat, an Irwin 54' looked pretty good. Just a lot of road rash, the dolphin striker pulled out of the boat, and a broken rudder. We passed on buying it back from the insurance company, but a guy bout it at auction for around $20,000. Since then it has had over $400,000 spet restoring it. While a good boat of the same year would cost 250-300. But as the work progressed they kept finding one more thing wrong with it....
On the other hand, a member of my club just bought a new j-22. It was at nationals this year and got T-boned. Went to Donnie Brennon (US Olympic teams boats right) for a $6,000
repair, and now the boat is in perfect shape.
To me it really depends on the extends of the damage, the cost of the
repair, AND the amount a comparable boat in good condition would cost. Sometimes free boats really aren't free.