I feel sorry for Robert.
I have been fanatical about trailering, while he has a history of tent camping. We started out tent camping, where he had a lot of experience. He was a boy scout; I wasn't. I followed his lead, and mostly stayed out of his way. The morning he broke camp and packed the car, while I was in the campground restroom was an epiphany for me. I bought a trailer. Now I was in charge of setting up camp. I knew trailer systems, he didn't.
I wrote my Checklist 8.0 so he wouldn't have to wait around for me to set up the trailer in the campsite. We go over it together now, and he has learned a lot about how the trailer's systems operate. He still has to learn more about how inverters work, because we do more off-the-grid (a.k.a. boondocking) trailering now.
We've been discussing a trip he takes every year, lately on his own, to a retreat. When we used to go together, we used the trailer. For the past 2 years, I have not accompanied him. He has used the tent (we still have it). We've discussed how he would be a LOT more comfortable if he took the trailer, and I encourage him to do so. Part of our discussions entail how we are both getting older. What would he do if I had a heart attack or stroke while out camping? (I take blood pressure & cholesterol medication.)
We decided that he needed to practice more actually backing the trailer into and driving it out of a campsite. We went up to Heartbar this weekend, where Gina D. is workcamping, and he was to do everything himself.
We are home now. There is "minor" damage to the front plastic bumper cover on the Honda Odyssey where the wheelwell contacted a wood bollard post going backward and tore the front bumper cover free of the body. The trailer's 4" Bumper/Sewer Hose Storage is bungied up on one side until I can repair the torn out mounting from backing into a large rock.
Swinging the car too wide the 1st time, caused the front bumper damage. Gina came by and told me to take her dogs to her campsite, and stay there, while she helped Robert, who was frustrated and ready to quit. He repeated backing the trailer into the campsite 8 or 9 times, circling around the loop between tries. He was frustrated that the trailer would keep wandering to one side or the other; and not go straight back in. He had a difficult time judging the depth of the site, and backed the trailer into a large boulder at the back end.
It was difficult for me to witness, but it was necessary for him to experience. We need to practice more...