My first boat was a Catalina 22 and I like it so much I kept it when I got my 30.
There are lots of them around in your price range and the pop top would make overnighting easier, though I day sail mine. The majority are swing keels, but I prefer the shoal draft wing keel. It's not as desirable for racing but you eliminate the maintenance issues of the swinger and you'll never notice the difference when cruising.
Check out "Chip Ahoy" Homeport
for just about any maintenance/upgrade question on the C22. You can often find a boat in your area by posting on Chip's email list. Also check out Catalina 22 Home Page
One important thing is parts availability. Catalina still makes the 22 and Catalina Direct sells just about any part you'd need for the boat. Catalina Direct: Welcome to Catalina Direct Online
. Subscribe to Chips mailing list and you'll have a built in tech support site for any project. You can't put a price on that.