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#2
RE: 96 Grand Cherokee for towing
My opinion is it would be like the tail wagging the dog. What is the vehicle rated to tow? Are you going to be pulling on flat land, or in hills? What is the tongue weight of the trailer? If it can handle it, I would strongly reccomend a transmission cooler.
#4
RE: 96 Grand Cherokee for towing
If that is as far as you will be towing, I would just suggest the transmission cooler, a good hitch, and a trailer brake system. If it is rated at 5,000 pounds and no hills, I would not hesitate. The hills is what would hurt you.