I'm not looking to 'make my money back' but rather to find a boat I can have a couple years of fun on while developing the skills I'll need on a 30+ foot boat. Some of the skills I need to learn are repair and renovation as I will probably never be able to afford a new boat and there are so many sound but ugly boats out there. I know that when I have a couple grand to spend I'll be able to find a Catalina or MacGregor 22, they are all over the Tampa Bay area within my price range, many such as the 1985 Catalina I posted above needing little to no work immediately. I really like the layout of the Kittiwake, most boats that size don't have a nav station or a full keel spade rudder that draws 3'. It's a little older than most of the boats I fantasize about, I generally try to stay in the late 70s early 80s fiberglass boats. I really appreciate everyone's input, I understand it's easy bite off more than one can chew when it comes to total renovation.
All that said I would love for someone to chime in for the other side and list some of the pros of buying a blank canvas; perhaps some intangibles that might outweigh the financial cost of the repairs I mentioned in my first post