I can answer this... when I got my first trailer, a Casita
in the earlier 90's I was bad bad bad at backing up and avoided it at all costs. It wasn't from lack of trying or lack of learning but lack of ability... On my first long trip across country with my mom and her Yorkie who never quit barking, we got a late start and I was grumpy... after a few hundred miles we decided to stay in a motel in Palestine Texas instead of going to a campground. I thought the driveway was circular, it was not. For the life of me I could not back the trailer out. There were cars parked on both sides of me, I could barely go forward and ended up with it jack knifed, in the pouring rain, in the middle of the night with a frantic mother and a barking dog.
After ,many attempts we ended up having to call a tow truck and the driver laughed at us and got in the car and backed the thing out easy peasy. Charged us $45 bucks and sent us on our way. My temper was flaring to the point where I just decided to drive on through the night and onto the next.
Moral of the story.... always have a wheel on your jack... if that Casita
had had one I would have unhitched it, spun it around by hand and rehitched it to the car. I have insisted on one ever since. I am still not good at backing but I check to make sure I am never going into a dead end and I practice backing up all of the time. Some people get it, some don't.