This last year I purchased a coastal cruiser. In deciding which boat to buy I read everything I could get my hands on. One book was a thorough discussion about yacht design and was organized by type of use, daysailing, racing, family cruising, ocean voyaging. It also had a huge matrix containing more variables than you would think existed, but also some very important ones for me and I incorporated them into my decision tree. I wanted a strongly built hull and deck with robust
rigging, head room (6' minimum), medium displacement, good speed capability, a favorable capsize ratio (should I make a very big mistake at the wrong time) and a fairly high comfort factor for two on board. I wanted to be able to single hand and live aboard for a couple of weeks. No outboard, no deck stepped mast and no swinging keels/centerboards, etc. And it had to be available for $10,000. I ended up with a 1976 Pearson 28-1, have replaced
rigging, and lots of other stuff, am still under $10,000 and have one hell of a boat with a lot of potential for coastal cruising. Everyone that comes aboard my boat is impressed with its size, its comfortable, airy and open cabin, the cockpit size, and I'm impressed with the way it sails. I used to have one of those really classic looking boats with a long keel and attached rudder and I've got to telll you that a fin keel and spade rudder is the way to go if you need to do more than make long straight runs in open water.
Hope this helps, and good luck