You're talking apples and oranges. A log truck or a building material rig with a Spyder forklift hanging from the back of the trailer are Class 8 heavy trucks with trailers DESIGNED to be loaded that way. The OP is asking a question about towing a small utility trailer, loaded with a farm tractor, behind a pickup truck. (even if it is a 1 ton)
Also, it's not the overhang that's the problem, it's the balance of the load. If the trailer is tail-heavy, or even too tongue-heavy, it can become uncontrollable, regardless of whether or not it is overloaded.
Ya'll make up your minds.
Is the massive tongue weight going to destroy the back of the truck or is the (minimal if loaded properly) overhang of relatively lite attachments going to make him lose control?
I'm going to give the OP enough credit that he can get the weight of the tractor somewhere near the middle of the trailer........
I'd put that 50HP tractor (with no implements) behind my 1/2 ton on a no brake 16 foot utility trailer and haul it anywhere I wanted to go on a flat, two lane highway.