I am sorry, I did not read all the comments, that said, How about the boy finding an old farm truck in a field, and getting it fairly cheap. (That is what I did with my 55 and 58 Viking 60 2-ton trucks).
Like John mentioned above about a "bad idea" it reminds me of pulling my 58 2-ton home with my 1/2 ton Suburban. Suburban weighed 5500#, the 58 viking, 9,000#, total with truck and trailer 17,340#. Did it go, yes. Did it stop, well, yes, but not real nice (the brake on one wheel on the trailer grabbed sooner than the others!) was it a long ride? YUP! I would not do that on a regular basis at all! Horses would have been traumatized to say the least!
I pull my 35' vintage trailer with the 58.It has a newer V-8 in it. (1967 327). I pulled my trailer home to Seattle from Montana yesterday with it (long story). Roads were compact snow and ice for the first 100 miles. Yes, the trailer is not as heavy as the 3 horse trailer in the first post, but as suggested, for the story, why not also find a vintage horse trailer to pull behind it?
