How heavy is your trailer?
With the 2011 Grand Cherokee, the most common problem areas were the air suspension and panoramic sunroof. Both are avoidable options. With the 2014, problems have focused around the new infotainment system. These should be ironed out by now, but time will tell.
If reliability is a major concern, you should check out the Toyota 4Runner. In some ways it's not as nice as the Jeep, but they are consistently very reliable. I didn't care for the ride and handling of the SR5, but have been told that the Limited (with a different suspension system) performs better.
I liked driving the 2014 Acura MDX more than either of these. It's rated to tow up to 5,000 lbs. Though it has a third-row seat you probably have no use for, it drives much more like a good midsize sedan than either the Jeep or the Toyota. It will also be much easier to get into and out of.