Looking for some advice for our steep driveway

Those of us who grew up on a farm are having a good chuckle about this problem and some of the answers. OP, it will not be a problem as you have plenty of truck and you are not on wet grass which would make for a fun ride. Coming down your trailer brakes will automatically be on harder because of the down angle of the truck. I would take the WD off because of the transition to/off the steep driveway plus more weight on the back will help the rear end stay put.