3: Jeep Grand Cherokee
The Grand Cherokee has been marketed as a luxury SUV since the day it hit the market. With that type of recognition comes a luxury SUV price tag and also expensive repairs (via Motor 1).
The Grand Cherokee had an especially tough time during the Daimler years, as these vehicles shared many components with Mercedes-Benz. Transmission failure was all too common, and head gasket failure was equally frustrating to owners of these SUVs.