I'm sure this gets said in every towing thread, but having towed with 1/2 ton regular cabs, 1/2 ton van, 3/4 tons, 1 ton crew duallies, the more truck you have, the more confidence you feel. A 20' enclosed with a car in it towed with a 1/2 ton short bed would be pucker inducing for me, having the experience of how much better a bigger truck does. Not that it can't be done, just depends on how comfortable you want to be when going down the road.