You could use a piece of string that is equal in length from the pin box to the bottom of the tail dragger. Hold it at each point, and measure down to the bottom of the rear wheel from the point on the string that is shortest and tie on a light plumb bob right there with the tip just touching the ground.
If you know the exact height of your unladen hitch in the truck, get a stick that long and have one person hold that and another person hold the other end of the string on the ground. Move those two positions to simulate the backing up of the truck up the driveway.
If that plumb bob comes off the ground that would mean you are high centered between the tail dragger and the pin box and the wheels are off the ground.
Obviously, with a laden hitch, you will get just a bit more leeway, but this method should tell you whether it is possible or not.
If this seems unclear, send me a PM with your email address, and I will send you some pictures that may help explain it.
Mike
2012 Winnebago Impulse Silver 26QP
2005 16.6 Double Eagle
2018 Jeep Wrangler JK
previously Snowbird Campers,
Triple E Motorhome and Fifth Wheel