I own a 2014 Grand Cherokee Overland. Love it. Purchased new, 15k miles not one issue, has not been back to dealer as I do my own oil changes. There is a recall to flash the stability control, but I'm afraid to take it because it's been so good.
I'm 6'2" 190 and it fits me perfect. Lots of room. After much looking, it came down to the same two vehicles for me as well. GC looks better....the interior is awesome, drives better, and has better resale. The adaptive suspension on the overland is what made me gravitate towards that model. The v6 gas engine performs excellent with the 8speed trans. Haven't towed other than just using a hitch cargo carrier. This is mainly the wife's minivan equivalent. ....I like it so much is making me hard for a hellcat jgc for my dd.
Edit,my local dealer pearl in peotone will do invoice on one, ask for grant.