We had an 01 Wrangler SE (2.5L) with a 5 speed stick (1,000# tow capacity) and pulled a 1,000# pop-up tent camper without any difficulty. We had a class II hitch and were not required to have electric brakes. The Wrangler pulled the load well with the exception of mountains and steep hills where 3rd gear became a temporary necessity. Still got about 18 mpg. The short wheelbase was never a problem.
We now have an 04 Wrangler Unlimitedwith a 4.0L automatic (3,500# tow capacity) and it pulls our 2,000# trailer very well. This does require electric brakes. Still use a class II hitch. The manual mentions about not pulling anything with a face front of more than 25 square feet. Most pop-up campers, boat trailers, etc. fit that category without a problem.
This past summer in Canada we saw a Jeep Wrangler pulling a hard-side hybrid travel trailer that must have had a face front of 60+ square feet with a weight of about 3,500-4,000#. The owner seemed to not have any problem with it which makes me wonder about the Jeep limitations they post in the manuals. If anyone knows the Jeep "line" on Wrangler towing capacity and why we can't pull more than the limit and/or the face front limitation, pleasend along some information. Thanks!