Thanks to ALL for the suggestions. I'm keeping my eyes open looking for that good off-season deal for my starter boat. It looks like my off-season inventory choices within a couple hours of Indianapolis is fairly limited.
I did come across a couple other boats that I would like some feedback for my intended use. I have not had the time yet to go and see any of these in person. All of the following include trailers: 1975 Chrysler C-22 $4900 (swing-keel), A "year-younger-than-me" 1963 Pearson Electra $4500 (long keel, older boat is said to be in great condition, which is more than can be said about me..haha). SHNOOL, I did find a 1987 Hunter 23 for $4500, a 1987 Catalina 22 $5200. Each of these boats is advertised with trailer, outboard, sails, etc.