I've been both the entertainer and the entertainee as well.
This summer was the first time with my new trailer, which is only two feet longer than my old trailer, and I had a hell of a time parking it. It didn't help that both sides of the road were pure mud, so I had a lot less road to work with, plus there were people's cars parked all over the place.
I came at it from one direction first, and just didn't have enough room to turn without the back end hitting the trees along one side and the guy behind me, so I tried from the other direction and the damn fire pit was in the way so it was a bit of forward and back. Once I knew I was clear on both sides we got her parked.
My old Mallard 31T was so easy to park I figured, "what's two more feet?"
The entertainment this weekend was a guy that got in to some mud backing in and threw mud everywhere with the 4x4. Covered the front of his trailer pretty good. He handled the situation really well, it was the mud slinging that was the entertainment. Lots of cars parked everywhere for the long weekend, so he had no choice but to take it through the mud. Neighbors watching slackjawed instead of moving their badly parked cars out of the way. (There were times yesterday you couldn't drive down some of the roads in the CG because of where people parked!)