In my late teens I had a summer job on a farm that included having to back a hay wagon into a barn. I couldn't get the hang of backing a drawbar trailer at all, even with the agility of a farm tractor as the tow vehicle. By the time I'd un-jackknifed the wagon, negotiated the doorway and finally got it to the foot of the conveyor in the barn my two fellow student-farmhands were paralytic with laughter.
A couple of years later, reversing a College rowing club trailer full of (extremely expensive) racing shells behind the crew minibus was a much more daunting prospect, but I found its close-coupled twin axle much easier to work out. Although on one occasion, I think for a regatta in Wallingford, it very nearly ended up wedged diagonally across the entrance to a car park. A racing eight is about 62' long, and splits into two halves for trailering, so the trailer must have been over 30' long overall. I'd be terrified trying to reverse something like that today - oh, the overconfidence of youth!