Hi Forest,
Here is MHO based on actual ownership experience:
'88 Suzuki Samurai Cute cheap, go anywhere (new lifted suspension installed...big tires) Ride quality similar to a Ford 8N.
'96 Cherokee 4.0 5 spd manual. The base models especially are kind-a tinny but the mechanicals hold up well. Various details like window regulators and trim pieces have to be repaired occasionally. The 4.0 is a good engine ..especially in the fuel injected years. They are a bit small inside. I like the classic Jeep Wagoneer look.
'97 Jeep Grand Cherokee Orvis Edition. V-8, Leather, all the options .I loved it for 190,000 miles. Some of them have problems with the rear axle which can be remedied very easily if you know which parts to swap in. 16mpg :-(
Currently,,,2006 Jeep Liberty 2.8 CRD Limited. Not quite as nice as the G. Cherokee but comfortable and decent handling on and off road. 4 cylinder diesel gets 30 mpg hwy. I installed 1" wider wheels and tires which enhanced the on road handling. More aggressive tires are installed for winter travel.
I have towed all of these with my '78 Newell. They towed very well, barely affected the Newell's performance at all. Each of the Jeeps have had plenty of room to install an additional light socket into the tail light housing. I run the wires along the frame up to the front. It plugs into the Newell trailer light socket. All have been very capable for "light" off-roading. Lift kit and larger tires would be needed to achieve that same "look of horror" off-road.
web-sites you might find interesting:
http://lostkjs.com/
http://www.jeepforum.com/forum/index.php