Help deciding. New travle trailer.

Very interesting situation. If your GC is the current body style, it should be tow rated for, I believe, either 7200 or 7400 lbs. The hitch is a class IV, and check a Jeep dealer on this but I think that should be good for up to 1000 lbs hitch weight. Payload (carrying capacity) of the Jeep is an issue, though. The 5.7L V8 is a pulling machine, from all accounts. The Jayco and Winnie both run about 5000 lbs dry, and the Jayco is lighter on the hitch (525 vs 630) than the Winnie. They both are rather long, about 27'-29' overall. I say you will be ok with the Jayco, and possibly the Winnie too, IF you get a good weight-distributing hitch with built-in sway control. Something like the Equal-i-zer with 4 point friction sway control, or the Reese Dual Cam, at the least. A Hensley Arrow or ProPride would be better. Such a unit will add nearly 100 lbs more to the weight on the ball, though. And you should look to see where the TT's water tanks are located; a fresh tank 'way up front, if filled, is likely to add too much hitch weight. Thus I'd favor the Jayco for this reason.

The GC doesn't have a long wheelbase. That makes the sway control super-important, to keep the tail from wagging the dog. Plan to drive within the 100 kph speed limit and leave plenty of space ahead for braking distance in case of an emergency.