So went out today and tested how well my 2007 JEEP GRAND CHEROKEE 4X4 V6 3.7L towed a bass boat. The test boat was a 1994 nitro 898 which was loaded with 1/2 tank of gas estimated weight was around 3300lbs and the trailer was a single axle with NO surge breaks. I opted to use triptonic so that my tranny doesnt over do itself ( now i just have to learn what the good manual shift points are) and it pulled fine got it upto 55-58 MPH at 2000 Rpms and was able to accelerate moderatly if i did have to pass someone. Breaking was nice and if i go with a boat/trailer with surge breaks ill be fine. So all in all im stoked now i just have to shop around and see what i can afford around the 18-19.5 ft range

You'll be fine. Like you said, a trailer with brakes would be nice, but towing should be o.k. See if your Jeep came with a tranny cooler, and if not, it might be worth the little extra cost to have one put in to protect an expensive tranny replacement. Good luck.

Yes in fact it has a huge tranny cooler. it almost covers the whole radiator.

You will be fine.

With or without trailer brakes leave yourself plenty of stopping room.  Stay out of tight spots and you will have no problems.