The only trouble is going to be fuel usage. That would be a 477/534 gas motor. We had them on straight trucks in the 1980s. When worked real hard you can easily only get 2 1/2-3 MPG, average.
So you could easily be spending a dollar a mile just in fuel. You should be able to find the same size truck for just a little more money with a diesel motor.
Also keeping those old gas motors running right when they are only used seasonally is a real pain. Rotors and caps corrode setting. Plus the fuel goes stale and then they run crappy until you get fresh fuel in them.
The 5 and 4 transmission setup is rugged but takes more skill to drive. If you hire someone to drive you will find darn few that can shift a 5 and 4.
I would look for a diesel and a 13 speed. Easier to drive and less maintenance. I would avoid an older automatic. They can be expensive to fix.
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Today's Featured Article - Old Time Threshing - by Anthony West. A lovely harvest evening late September 1947, I was a school boy, like all school boys I loved harvest time. The golden corn ripens well and early, the stoking, stacking,.... the drawing in with the tractors and trailers and a few buck rakes thrown in, and possibly a heavy horse. It would be a great day for the collies and the terrier dogs, rats and mice would be at the bottom of the stacks so the dogs, would have a busy time hunting and killing, all the corn was gathered and ricked in what we c
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