He doesn't need to pump up hill, he is already putting the jerry can on the top of the tractor body when pouring it into the filler pipe.
Yes it would be more convenient to be able to leave the jerry can on the ground tho.
But less likely fit into the jerry can.
I do in fact have to pump out a 4" floor drain and use a low voltage bilge pump, but there aren't many small enough to go in there and they aren't diesel rated.