OP John - I recommend you check out the Catalina's, either the 22 or 25 footers. There are so many of them around you can always find a great one for a deal and parts are easy to get at Catalina Direct.
I found a good condition 1986 Catalina 25 with a great condition galvanized double axle trailer with near new tires for $6,200. The previous owner had added many upgrades.
My friend went sailing with us and ended up buying a Catalina 25 for himself for even less.
Whatever boat you choose, I think its more important you pick a boat in the best condition you can afford vs. the brand. Boats need a lot of work just to keep them going, no need to pile on a bunch of projects before you even get into the water.
My Catalina was in good enough condition that we sailed her as much as possible the first summer, I did not work on her, I only kept a logbook of work needed (except getting the engine 100% perfect). Its so enjoyable to just sail, meet the other sailors in your area and build your sailing skills vs. always tinkering and fixing things.
Good luck and have fun searching for a new boat!