For towing & freeway driving duties in your price range, if it were me, I'd look at SUV over Wrangler.
I'm biased towards the WJ, because both my neighbor ('04 Laredo) and I ('04 Overland) have had exceptional experiences. But all models of Jeep have their weak points, so best to look very carefully.
The XJ is another Jeep people rave about. I've read a couple of articles about the simplicity and low cost of swapping a 2WD to 4WD. This could net finding a very lightly used vehicle for cheap, and give you some mechanical knowledge along the way.
There are a lot of really good, and really bad vehicles on the used market. Looking at only three different vehicles is a crap shoot, with a high percentage for failure.
Take your time to read through web forums with sub forums on models you are interested in. Jeepforums.com seems pretty good for this. So you'll know the weak points to look for when shopping.
Then drive the models you like to narrow down your choice.
Once you have your model of choice, look at as many as you can, and take notes.
When looking at used vehicles, unless I see something that absolutely knocks my socks off, I employ the 24 hour rule. After finding the vehicle I want, I'll wait 24 hours before making the final decision.
Hth,
Good luck on this! :beer: