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M36's aren't the rarest truck out there but they are not all that common. You should not have any problem selling it if you decide to join the 5 ton club.
With the front of the trailer right up against the back of the cab there should not be too much overhang but there is already several feet behind the tandems. If you did not put a lot of weight in the rear of the box it would prob be OK. I would consider some type of DOT bumper in the rear to...