This reminds me of a guy who was trying to back a utility trailer into a driveway across the street. I don't know where he got this thing, but it was about 8' of trailer, then 10' of tongue on the front of it. Very responsive to jack-knifing.
Well, I happened to be outside waiting to get the kids off the bus while I was watching him try to back it in. He was turning in on the passenger side, but instead of crossing into the oncoming lane (sort of, you know how they're not marked in these sub divisions) he thought he could do it all from the one lane. Well no way was he able to do it. When he managed to put the tongue under his bumper on his third try I finally realized this is more an issue of an inexperienced driver than an just a guy who was having a bad day.
I tried to explain to him how to adjust his approach, by making full use of the roadway, but instead he just hopped out and tried to talk me into backing it in for him. Having worked with enough insurance companies over the years, I knew I was having nothing to do with driving his vehicle, but instead I offered to help him push it up his driveway if he unhooked it. It didn't look too heavy, just having a dog house on it and I figured that was safe enough.
Instead, he said he wanted to take one more try at it and went down the block to turn around. I thought he was going to try backing in from the driver's side to get a better angle, but instead he just turned in so he drove over his lawn and circled around to the driveway.
P.S. For the record, I can't back up my little 3' trailer that connects to my riding lawnmower more than 1' without jackknifing it either.