Follow up.....bought the GC. Been on four trips and pulls with ease. The GC manual does give you a limit of around 3400 lbs before requiring a WD hitch. I am right at that weight, did not do WDH and have no issues. A little frustrating how hard it is to find this info before buying the TV. Love the jeep, love the 277 and they seem to be a perfect fit.
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2014 Rockwood HW277
2014 Grand Cherokee V6 2WD
I was considering the GC as a replacement for my 98 4runner if it couldn't tow the 277 after we got it last fall. Well after 2 long trips up high mountains of both the NY Adirondacks and the Green Mountains of Vermont, I find my old camping truck still capable of doing the job. That's with a 5000lb tow capacity. So I'm confident you will have no issue towing with that Jeep. Enjoy your trailer, it is amazing.