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Well, I did it. After lots of advice from people on this site and lots of shopping, I came accross a 1984 Outrage 20 with a 185 hp Johnson in good shape for the right price.
The boat is pretty clean and the wood is in good shape. The motor runs good too.
I know I talked about 25 and 22 footers, but for my first boat, they just seemed too big. For now, this is where I want to be. I'm a great big old happy boy.
My girlfriend loves it too. We will be keeping her 1966 13 footer that is also in nice shape. I'll be putting up some pics soon.
Thanks for all of the help guys. Hopefully all my questions helped others make the right choices. And I'll try to document some of the work I do on it.