I think the Cherokee looks ok (not great). It is certainly a bold polarizing design.
In this group, the back of the CR-V, front of the RAV-4, Tuscon, Forester all look questionable at best.
I would not buy a Chrysler product, because of concerns about reliability, especially with the Fiat sourced 2.4L engine. However, this vehicle can be equipped with a real low-range transfer case, under body plates and locking differentials. It is significantly better in this regard than anything in this segment.
The 9 speed AT, on the other hand, is clearly there for fuel economy. While driving, it constantly shifts which is something you may need to get used to. For people who think about towing, the larger V6 and towing package along with this transmission can get you 4500lb of towing capability.
Personally, I don't need any of these capabilities, I do wish the CX-5 has a diff lock option (similar to the RAV-4, Rogue), but otherwise the capabilities of the CX-5, fun to drive factor, fuel economy and looks are right for me.