One more thing, never just say "Cherokee" the new Cherokee is offensive to the Grand Cherokee lol. Other than that you will love your new Billet Silver Overland. One more thing, if you decide to off road any, you want may want to consider the 4x4 version.
For light offroading, the 4x4 will probably do nicely.
If your offroading includes big bumps, water, and such, you might want to look at the Off Road package which includes skid plates and the ability to lift the entire vehicle via the air suspension.
Dunno about your area, but 4x2's may be a bit lower in resale value than the 4x4s.
As for your original question, the early 2014s had a few teething problems, with the earlier the build, the more there were in general. In particular the UConnect hardware on early units appears to have been sourced from the Kmart disposal bins.
By summer, this appears to have been much better made, and allegedly the units built after late August are more like any other new car from anyone including the premium brands--you can have troubles but they are far less likely.