The Cherokee leather seats are really nice. We have a loaded Trailhawk. However, the Limited or Latitude would be a better fit for you. As mentioned, towing 4 down is drivetrain specific. I think the Cold Weather package with leather has heated REAR seats. The self parking works. I've used it one time.
I have a difference of opinion on Ford Sync vs Uconnect. Ford Sync has always been buggy. It may or may not work. When the Sync does work it's subject to crashing. Friends/relatives have severe problems connecting their phones to Sync. Bluetooth pair usually requires a trip to the dealer. Chrysler Uconnect is about as simple as my Honda Civic. Uconnect just works. Recently had a 2014 Ford Fusion rental car for a week. The infotainment Sync system was rubbish.
If you have a smartphone built in Navigation is not a big deal. On the Trailhawk, it's cheaper to get the towing package from the factory than aftermarket. Not sure about other models. The moonroof is nice, but, not necessary. Whatever it takes go for the heated steering wheel. The technology package includes sensors all around the vehicle. These sensors give blind spot assist. The same sensors can be used for slow parking lot assist. The sensors will tell you approximately how close you are to objects. Very handy for Starbucks maneuvers.
Did not buy the vehicle to tow 4 down.
