Flat towing the jeep will not be as bad as a trailer would be, Due less weight.
We flat towed a CJ from Asheville to Charlotte with a two door 96 explorer V6 AUTO, And you could hardly tell it was back there.
I tow with a 99 Expedition 5.4L and a 16' Hudson Trailer, I have a TJ that weighs 4k~, I have dual axle brakes on the trailer, and if I am not careful it will push me around (paying attention and braking early). Oh and SUVs don't have to have weighed tags.
Another thing to consider is fuel, Not sure how the Dakota will do on Fuel Mileage, my Rig gets an AVG of 9 MPG when towing. Might consider that when deciding to rent or buy a trailer.
Just some thoughts
