I had a similar issue when I picked my boat. My criteria was a little more focused even... i wanted a simple non-swing keel. Which is why I have the cat capri 22. I also wanted something that had all the sail controls of a racer, but some comfortable overnighting berths.
But, in that price range... using the JIMMY as your tow vehicle constraint (as the JIMMY is an S-10 with a body), so you are probably limited to #4000 max.
Cat 18 fixed keel
Cat 22 swing or wing keel
Capri 22 wing keel
Hunter 23.5 wing keel
Hunter 22 swing keel
S2 (racer) - if you are only going to use the 1/2 ton truck
Mac (us sailors like to pick on the mac, but there are still a helluva lot of them out there)
Compac 19 (or 23 if you use only the 1/2 ton truck)
Precision 18 (or 23 if you use only the 1/2 ton truck)
J/22 is a pain to launch with anything other than 1/2 ton truck.
My wife and I do a lot of towing. We have horses, and of course the boat, plus we used to own a camper as well. Honestly the big deal with towing isn't really the weight, it is the surface area of the thing being pulled. IE: the boat sits high, and would significantly CLEAR the JIMMY, but the 1/2 ton (depending on model) would sit higher and scoop the wind better. Trust me you could be at half cap of towing for the Jimmy, if that boat sticks up high above it, it'll make trailering an unhappy experience.
Compac if you want a great cruiser
Hunter compromise of cruiser/racer lighter
Catalina compromise of a cruiser/racer light
Precision compromise of a cruiser/racer lightest
Capri/Starwind/S2 if you want more racer than cruiser
J/22 if you want a racer.