Flat towing up inclines

I am in the process of getting my Jeep ready to flat tow. I currently keep my TT at a storage facility that has a large inclined driveway going into the facility. I see many gouges in the road from trailers and motorhomes trying to take a left turn straight into the inclined driveway. I always approach from the opposite direction so I can turn in at an angle to go up the driveway. My current TT is a low rider and I come very close to bottoming out when I leave or enter the facility (even when I come in diagonal). I have never flat towed behind a motorhome before but I am wondering how the 4 down setup will handle coming in and out of the facility. I was thinking that I could drive the Motorhome and have my wife following me in the Jeep down the street to a Walmart that has a large parking lot to hookup. But then I think about all the times I have run into a large inclined driveway going into gas stations on the road. I am assuming the tow bars will twist and turn and adjust to this. I might be worrying about nothing but I am curious to what other peoples experiences with towing up and down large inclined driveways from the street.

Burch