Well, Monday will mark two weeks since delivery and over 800 miles on my Overland. I've lived with it long enough now to share some reflections on my experience.
First, by way of background, let me say that my personal experience with SUVs began with a 2007 VW Touareg. That vehicle had a reputation as being unreliable, particularly the electrical system; but I took a chance because of the quiet and comfort (I'm 6'4" and the VW turned out to be the most comfortable vehicle I've owned), and I'm glad I did. In over 100,000 miles, the only time it was in the shop for other than routine maintenance was when a horn went defunct at 85,000.
In 2011 I was ready to replace the Touareg with another one, but had a head-turning experience when I passed a new Grand Cherokee on the highway. I discovered the Jeep had essentially all of the features of the Touareg plus some, and that the Touareg was being "dumbed down" at the same time it was experiencing a huge increase in price; so I was an early adopter once again and opted for the Grand Cherokee Overland. Turned out there was a problem with the rear hatch opening randomly even as I took delivery and drove out of the lot. Four visits to the dealer later, and on the verge of invoking the state's lemon law, Chrysler found a solution to the problem and for the next 58,000 miles, the vehicle was pretty much trouble free. The seating was not quite as comfortable for me as the Touareg, but not bad; and the Overland's other features more than made up the difference.
Almost four months ago I decided that my V6 was inadequate for towing our camping trailer efficiently; to do the job well I needed a V8 or diesel. I opted for the latter, placed an order three days after Chrysler started accepting them, and then began the wait. The 8-week delivery estimate ultimately stretched to 13, for reasons that readers of this forum will be familiar with; but my 2014 Overland did arrive, I've driven it, and here's some of what I think:
Fit & Finish. Frankly, it's not the equal of my 2011. I must have gotten a "Friday edition," because several of the trim items, both interior and exterior, simply were not fitted and secured properly. Examples include an exposed, irregularly cut carpet in the front passenger's footwell, a panel missing fasteners and flopping around in the driver's footwell, a detached piece of interior trim around the window in the rear hatch, and a poorly aligned fuel door--and there are others. Nothing huge, I guess, but not what I would expect of a $50,000 vehicle. In contrast, my 2011 had no such issues. Neither do I consider the paint job the equal of the 2011
Mechanical & Electrical. So far I think there's nothing major. I have the power tilt steering wheel set to retract when exiting, and it has developed quite a grinding sound when it nears the end of its travel. It will be looked at next week. There have also been a couple of UConnect issues, but nothing that probably can't be fixed by software updates.
Things I would Change. If I had my druthers, there are a few things from the previous generation (i.e., 2011-2013) I wish that Jeep had carried over. I wish they had kept physical switches for the heated seats and heated steering wheel; I wish they had kept the ability to display estimated arrival time, miles remaining, and elevation (altitude) simultaneously on the same GPS screen; I wish they had kept a USB port in the upper console compartment; I wish they had used something other than gray to display the transmission-selected gear number while in drive (D); and I wish they had used larger font sizes on the touch screen (I'm 20/20 vision, but the programmers must have been 20/5! They appear to have been more interested in classy appearance than readability, particularly in bright reflected light during the day). I also wish they had kept the black wheel well trim and black lowest side panel on the Overland (I travel a great deal on gravel roads, and the painted trims pieces just get beaten up, even with splash guards).
Finally, and this is a big one for me since I am so long-legged, I wish the shifter had not been moved so far left, and that something other than a t-handle had been designed. In my 2011, I could comfortably rest my leg against the center console while on long drives and/or using cruise control. Now, an area just above my knee strikes the t-handle, and during longer drives it can become very painful--some sort of padding becomes necessary. A very short test drive does not readily reveal this problem, but I wish that I had discovered it before buying--it might have been a deal breaker. If you have long legs and are accustomed to resting against the console, be sure and check this out.
Dealer Preparation. In my case, dealer prep wasn't great. DEF tank was less than half full ("we don't have any"); the fuel tank was filled only after I asked; I found out later, while on a trip, that the windshield washer tank had not been filled; their were still a few scraps of the cellophane-like protective covering that had not been removed; and there were black marks on the driver door and front passenger seat.
Summary. Despite the disappointments described above, I still consider the Grand Cherokee to be best-in-class for the price. The diesel engine and 8-speed transmission are all I hoped they would be and I'm getting great mileage. I'm not aware of any other similarly priced SUV of its size that offers such good towing and off-road capabilities.
If my GC is at all typical of the 2014s, I certainly wish Jeep's quality control were better; but assuming that the items mentioned above can be satisfactorily addressed, it's still a "keeper."
Sorry this was so long, but I trust it is helpful to others considering this vehicle.