Lol... yeah I pull my hopper bottom in and out of worse than that in most of my best entrances, no way I'd be worried with a tractor and wagons.   I have one field that the entrance to the road is about 50 feet long, and steep enough you are a little winded walking up it, and I take a single axle semi loaded out of there when it's dry enough to pull it.  Otherwise I climb it with a loaded grain cart several times.