Another thing to keep in mind is the laws of the state you are driving in concerning the lights. In some states, the dolly lights must be used, because of the distance between the side of the car and the dolly fenders. The car must have lights or reflectors on the rear because of the distance between the end of the car and the dolly lights. Reciprocity probably does not apply; just because you are legal in your state does not mean you will be legal in all states!
We towed our PT cruiser from Billings to Chattanooga and back, on an old Demco dolly. In all RV parks except one we got a pull-through site. No problems.
The Jeep, of course, is towed four down.