The 1999 Jeep Cherokee Classic is a very utilitarian vehicle. It is a bit loud on the road, does not have the best gas mileage, and the six cylinder engine is adequate. That being said, there have been absolutely no major issues and the vehicle just keeps running.
Four wheel drive is an excellent feature for Wisconsin winters. The body styling is, as the name suggests, classic.
The gloss painted bumper of the Classic is not conducive to hauling as anything slid over the bumper leaves scratches in the paint. The interior is not roomy.