Old Lady & tow dolly. Can this relationship work?

We used a Demco SS to tow our VW. I installed longer safety chains that allowed me to thread them through the wheels without having to lay on the ground. With that simple mod, I could drive it up, attach everything without getting down on the ground.
As far as moving it, that was pretty simple and rarely necessary. We use pull through sites as much as possible and if it's a back-in, we either just push it back or leave it attached and back in.
Good luck,
Gary