After looking at, reading reviews, and driving both the Grand Cherokee and regular Cherokee, we bought a CPO 2019 Cherokee Trailhawk. After driving, it was an easy decision for us. It will be the wife's primary car and giving up her beloved 2017 Ford Escape wasn't going to be an easy sell, but she loves the Cherokee.
To be honest, all the knocks I heard about the Cherokee (jerky trans shifting etc) we found true in the Grand Cherokee we drove and not at all in the Cherokee. It drove just fine and for me, and I just felt more comfortable in it. For her, the GC was too big, and the Cherokee was a familiar size. I know we are giving up some off road performance, but we are mainly towing it behind the motorhome and using it for forest roads and such, not anything hard core so it will be fine.