I'm actually on my 3rd Grand Cherokee, having owned a WJ and WK previously. The interesting thing for me, as I think back when I purchased my 08 Limited, is that I never had any regrets when moving from my 04 to the 08.
I can't say the same about my 14 Limited. There is plenty to love - the styling, the 8-speed auto, how it pulls my camper (significant improvement over my 08, and both have/had the Hemi), the technology, etc.
I didn't think I would, but man I miss the flipper glass!
I can live with the so-so audio (my 08 was much better). I haven't seen too many discussions here (maybe I haven't looked hard enough), but the lack of the front limited slip differential is one of the things that I miss the most. My 08 would drive circles around my 14 in the snow and mud. Maybe I haven't gotten used to the electronic intervention in the 14 yet, but having all 4 tires slinging mud sure felt better than the darn brakes kicking in up front and bogging down the motor.
Would I take my 08 back in place of my 14. Heck no. Kind of wish I would have held on to my 08 though and kept it for my offroad toy!