One of my stupider moments was when picking up a tractor, using a friend's rear wheel drive van and a rented trailer. The trailer was set up for the wheel width of a standard car so the tractor wheels were very close to the inner edges of the ramps. We chain tied the tractor to the trailer.
Something just didn't feel right about the road that we took to the seller's location. It was very rolley and some sections seemed very steep. It had just been re-graveled, and the rock was loose and several sections crossed land bridges across small valleys. The shoulder's dropped off steeply into the valleys. The seller said that the road was the only way in or out.
We were heading down hill just before the last very steep section, I told the friend that he better speed up or we'll never crest this hill. He didn't speed up and 3/4th of the way up the hill his van started to spin the tires. The van stopped and then started sliding backwards towards the shoulder. He set the parking brake, as we continued to slide and said we might have to jump out.
I could not accept losing my just bought tractor, paying for a wrecked trailer, and my friend loosing his van. I ran back to the trailer, unhitched the front and back chains, started the tractor and backed it off the still moving trailer. Soon as the rear tractor wheels got on the ground, everything stopped sliding. We were about ten feet from the shoulder and the drop off.
With out the weight of the tractor, my friend could drive up the hill. I followed him till there were no more hills and we re-loaded the tractor and got it to my place.
This could have gone so very badly.