Welcome!
Need more info on the Jeep - year, model, engine, rear end ratio, and if it has a factory tow package or not.
Your 5000# limit should be the maximum loaded tow weight, not a fictitious "dry weight" listed in a sales brochure. My new TT is 300# heavier than the listed weight due to the options.
You'll need a weight distribution hitch and brake controller no matter what you look at except for a pop-up.
With the short wheelbase of the Jeep and the weight limit you'll be looking at trailers no longer than 25' or so.
Local dealers are Camping World, Wilkins, Ballantyne, and Johnstons RV. We looked at them all and hit the trailer shows at the Dome, Sports Park (Elmgrove), and Syracuse. After having a hybrid for 7 years it still took us a year to find a new TT that had most of what we wanted.