Trailer access calculation?
I would print off a satellite (Google) image of the drive in question. Then cut two scraps of correctly sized pieces of paper representing the car and trailer. Use those to play "drive the trailer home".
About hitting the tail of the trailer, we all do that. That's why glider trailers have skids in that back. To minimize this get an extra long/low tow ball adapter. This will raise the tail.
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