The first trailer tow I did was a small RV, which I had to back into a slot that was behind my corner garage. After entertaining the neighbors for some time, one of them offered to guide me. That didn't work either so I asked him to do it. He hit it the first time. At the next opportunity, I took the trailer to a parking lot and spent hours practicing turning and backing around buckets. It is a nice skill to have and the confidence really makes a difference on the road. I also learned to pay attention when parking for a way out of the spot. Every trailer is different and short ones are particularly difficult because they jack knife so easily.
As you said, Tedward, it is not a direct comparison, but an example of how new experiences will lead one to appreciate the unsuspected difficulty in doing something new, even when it is a familiar activity that others do every day. Now put that into novel activity in a completely different environment and it is no wonder that NASA completely misunderstood what was needed to do orbital rendezvous and EVA requirements on the first try.
My new RV (when it arrives) is the same length as the old one but is lighter and we widened the driveway so that the backing path is now fully paved. Parking should now be a breeze.