Thank you for all the feedback. Very much appreciated.
Looks like it's a no go, so will look into other options.
Basically, there's space about the length of the trailer (with a bit of room to spare, and about 6 feet wider. I can easily park the trailer in reverse, but then trailer door would be facing a fence and would not be (easily) accessible. Parking head first, there's no way to fit another car length wise or enough width get the car out by the side of the trailer.
Looks like a power dolly would be my best option. Will also look into the possibility of a manual dolly + winch.
Again, thank you for all the help. If anyone still comes up with a creative solution for getting a trailer, head first, please let me know ;)
