This is a great idea and I say this partially because I am in the process of doing the same thing. I am 25 and just bought my boat, a 1981 30' Lippincott. I got it for 8k because it has been sitting and the sails were shot, but the interior is immaculate and all the systems are in good working order. It has been a bit of elbow grease to get cleaned up, but my survey came through to value it as it sits at 14k so I think it was a good deal. Basically I will be out the door at about 15k with a really solid boat that will be of the value. This being said I took 2 years to find the boat I wanted and to buy it. My advice is look at what you want in a boat and see if any really spark your enthusiasm, this one to me screamed buy it and that is whats important that you love what you buy. I also read Nigel Calders Cruising Handbook which helps lay out what you want in a cruising boat, why different things are good, and how they work. With this I narrowed down my search because I knew nothing of all the different brands, but this let me pick out attributes and see who fit the bill.
I was also looking at this boat which is know is a bit out of your way, but the price seemed really good for what it is and it has been on the market for quite a while, if they didn't take the offer on the boat I bought this was my next offer.
Bristol Centerboard Sloop
Well I certainly wish you the best and make sure to keep us posted on the progress.