The engine compartment is pretty tight. After driving the truck I don't think I would choose to put in a 371. If you want to go Diesel I would go with a cummins 5.9L or something similar. The firewall is a bit different than a stock pickup firewall but not much. They also put a thermal barrier on the inside of the cab to deal with the heat of the engine. The engine sounds cool as can be under the hood but it just does not have enough power for the amount of work I can imagine it would be to migrate to that diesel from a 1950.
My dad is thinking of having it painted. If he does I will take some detailed pics as we will be tearing the body off the frame and taking that to the painters (that way we can fix the transmission easily and re-do all the wires/cables. From everything I have found online this truck needs some documenting so I will try to make sure we have a photo record of everything we do with the truck.