We have a 99 Cherokee 4 door as one of our daily drivers (same engine as you describe, auto transmission). When we had a pop-up several years ago, we towed with the Cherokee. It was a 1022 Starcraft with rooftop AC. Not a big pop-up, but not tiny either, double bed and queen bed. It had a 10' long box when closed, single axle, less than 5000 lbs.
Dont tow more than a pop-up of the above size with the Cherokee. It has power and will not overheat, but the short and narrow wheelbase of the Cherokee does not lend itself to a bigger trailer. We had to use very long mirror extensions to see past the pop-up's width and a longer or taller trailer would have caused excessive sway. It dropped the MPG fron 21 down to 13 when towing and with two adults and one dog in the Cherokee.
Robert & Nancy with "Murphy the EOG"
Murphy has passed on, but Micah and Bogie have assumed the watch! 02 Holiday Rambler 5ver, 2015 Indian Chief Vintage. 98 Coachmen truck camper.