Doran, I've had all kinds of Jeeps since I was 16 yoa and the last few I had was the Cherrokee, I sold my last one just about three years ago because I started pulling 5000# boats
You would not Believe all the boats I've pulled. or even how far with my last two cherrokee's, and sometimes two in-line, a 1996 and a 1998 with that high out-put 4.0 motor with absolutely No Problem with the motor Or the transmission. That little sucker is 225hp and gets 15 / 16 mpg in town, 21 /22 highway, pulling the boats were all different but still pretty good. Once I pulled a little house, 20ft long 8 1/2 ft wide, on a 20 ft car trailer, 180 miles to my sisters house, that was my grandparents first house, we moved to Okc when we sold the farm.
The only thing I was really causious about is the overdrive, I never pulled a boat in overdrive, unless it was a lighter boat and I never try'd to keep up with traffic on hills, winds, or hot temps. Just One Thing ... the trailer you pull needs Brakes, I got a story in Dallas Tx. about that .. you Need trailer brakes.
Oh Yea .. I sold the 1996 when it got to 200,000 miles, and I sold the 1998 when it had 277,000 miles, and my buddy's dad is still driving it with well over 300,000 miles on it and has yet to spend any money on the motor or trans, other than regular service stuff.