I back in unless I am with Py in an irritable mood. Having worked 15 years on the crisis team, I am a fan of a quick getaway.
I've had neighbors, partners and my mother all ask me to park their cars. I can back in a 20 foot U-Haul but it would take me a long time to back in with a trailer. I've only had to park a trailer once, and that was a long time ago when I had more confidence. I was moving from NYC to Albany and they had no 20ft trucks left so I got a 16 foot truck with a little trailer and parallel parked it with no trouble. The sad thing was that we managed to get everything into the truck so I had to drive back to the UHaul place (from Brooklyn to Manhattan) to drop it off. Once we were out of the city we discovered that the speed limiter was stuck on 45 mph. There was no place that could fix it without a day's delay, so since Albany wasn't far, my partner and I and the cats suffered through it.