One night in November a few years ago,I rode with a friend to go get a truck in CT he bought--he used his pickup & car trailer to haul it home..
The truck was next to a barn,off the road about an 1/8th of a mile at the end of a long driveway,with tall trees along the entire length...single lane drive,with no room to turn around once you got all the way in there..!..pitch black too,no lights to guide you to along the driveway,only one outdoor flood lamp near the barn..the back up lamps on the truck were not much help either..
Attempts to back the trailer in was futile,with the owner of the property trying to guide us in with a flash light--trailer was about as wide as the driveway,and each side had a two foot deep drainage ditch all the length of it..my friend wasn't too good at backing a trailer up period,even in daylight..it kept wanting to drop into the ditch..
We ended up un-hitching the trailer after about a half hour of not getting anywhere,we made it maybe only150 feet off the road,and the guy suggested we use his riding mower to pull the trailer all the way to the barn,then fought with it trying to spin it 180 degrees by hand,so we could point it back towards the road...
We had to drag it sideways with the riding mower to turn it around..made some deep ruts in his driveway,which was mostly mud with some gravel mixed in..it had rained hard the day before,and our boots sunk up to our ankles in muck..feet got soaked instantly..

..was about 30 degrees out too..
We got to the guys house about 7 pm,it had been dark over an hour already by then..it was almost 10:30 pm by the time we had the truck loaded on the trailer,and strapped down..had to do it mostly in the dark,as the lone flashlight we had with us had its batteries croak almost instantly once we got to the truck..
My friend vowed never to go pick up another vehicle after dark..
Luckily we made the 50 mile trip back without any other problems,like a flat tire or other woes..
He has hired a ramp truck a few times to go get a few other vehicles since,when the owner wasn't going to be available during daylight hours ..said "It's WORTH the $150"...