I appreciate all the input. I do realize that I could easily be sinking a lot of money into something that is not worth it. As far as being up for a Darwin Award for just myself and my friend going out and learning how to sail, I do not see how it would be so dangerous. Lake Pontchartrain is really calm, large enough to be able to avoid anything and we would have a small outboard on the back if there is trouble. I would also plan on installing a VHF radio and a GPS. I actualy work on electronics on boats in the Coast Guard, I was stationed on a ship once, but it was nothing like a sailboat. By the way reading around and talking to some people that is exactly how a lot of people learned to sail.
We are just looking for something to learn to sail on, we figure if we spend a $1,500 or so each and we have fun and learn to sail, if it last 2 years it is worth it. Before I buy a boat I will definatly look into how much it will cost to have it surveyed. Which brings me to my next set of questions....
I went down to a Marina after work today and saw three boats for sell, the one I am interested in is a Catalina 27, I am not sure of the year, but from looking at pictures on the internet it is mid seventies. The sign said make offer, I called the guy and told him I am really new to sailboats and he said a couple grand, leads me to think I could take it for around $1500. He said it has 2 year old sails, I guess that is fairly new, I do not know how long they last. He did have nice looking covers on them. He also said he has the job sail at home. It needs a good cleaning. The outboard is locked up, he said it got about a foot of water inside it during the hurricane. I peeked around it a bit, but felt uncomfortable really going on it without him there. Well I guess a used outboard around a grand or so, so total invested $2500. It does not seem bad to me. Is 27 to big to learn to sail on? Will a 15-20 hp outboard be enough? I tried looking them up on the internet and alot of them have inboards that are 30 horse. I think the boat needs a little work, but it does seem like something that could be fixed up reasonably.
As far as having the hands on, knowledge working on sail boats, none. I have a 78 Malibu I bracket race, that is more my thing. I work on small engines and smallblock chevys. I can weld, which I guess I would not be doing on a sailboat, but I am definatly a hands on able to figure things out and fix them guy.
I am going to look around some other marinas, I just want something to last at least two years and learn on, and potentialy be able to stay a night out on once or twice. Any input on an older Catalina 27? It does not seem a whole lot cheaper than other ones I see listed online.
BTW, thanks for the links and suggested reading, I will definatly check them out.