If it were me, towing a car that big over a long distance would be a job for
something bigger than a Dakota. Think 3/4 or 1 ton truck. I'd be willing to
bet that the '55 Pontiac wagon weighs close to 5000# by itself, and a
suitable tandem trailer capable of pulling it will weigh approximately 2000#.
The trailer will definitely require brakes - if they are electric, you'll
need a brake controller. If they are surge-brakes, anything will do. Check
the ratings on your truck and hitch, and make sure that they are rated for
the type of weight that you are thinking about pulling. Then get a dually.
My $0.02.
Steve M.
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