The Cherokee v6 has similar HP and torque to my '08 Highlander's v6. I have towed for about 120k miles (out of 160k on odometer) with this vehicle and the drive train has held up well. (Several fluid leaks in the past 9 months, though.) In addition to the KZ Escape TT (2700 lb), I towed many miles for work with a 6x12 enclosed cargo trailer, up to 3800 lbs. I've taken the TT through the Rocky Mountains several times. The long grades necessitate 3rd gear and about 40 mph.
The Cherokee should do well with a TT of 17' or under, if you make sure your tongue weight is not too high. Keep the tongue under 400 lbs if you can (dry hitch weight no more than 300, because your LP, battery, water, etc will add to that). You would do best with a molded fiberglass trailer like Scamp, Casita, Eggcamper, Lil Snoozy, etc due to the smaller frontal area (they are lower, narrower, smoother, and rounded on the edges). But stick built trailers like my KZ should be ok as well, if you don't mind keeping it at or under 60 mph most of the time. If I go 65 I hear my HL's underside flexing (the sound is similar to stones tapping tin).
Have you compared the price of the Grand Cherokee? Similarly equipped models aren't much different in price, I think, and the GC has much higher tow and hitch weight rating. Personally I am looking at replacing my HL this summer with a GC diesel.
