Re: Prospective sailor.....
If you have sailed before (seems you have) and you're planning on a mooring or a slip, go bigger if you can. There are plenty of Catalina 27-30 in the sub $20,000 range. A 27 can go for around $10,000. (One on Ebay in NY for at $1,200 right now) If you're looking at gunkholing, consider a shoal keel, or swing keel. Then get out there. These boats can be singlehanded, if that's an issue. Don't be afraid, be cautious.