I stayed all night at the motel 6 across the road from Banister Mall one night. Stuff going on in the parking lot all night. Hookers banging on my door. Yet I'd often see campers overnighting it in the Hyper Wal-Mart across the road quite often. Know your surroundings, especially in the urban areas. -Or have armament ready.
I would think a landowner letting complete strangers boondocks on his property would have more of a risk than the boon docker would from the property owner.
It depends on how well prepared you are to fend and defend yourself. Common sense and safety precautions are always paramount.
We always have contacts that we let know exactly where we camp or overnight and once on the road again, we text which direction and route we're on. Should anything happen as in accidents, etc our contacts can give the police a trail to locate us. Quite like a flight plan.
Gbopp has it right -- if the host is named Norman Bates, keep driving. If you hear scary music, keep driving. If your hair stands on end, keep driving. If the bobblehead doll on the dashboard turns its head in a complete circle, keep driving.
We're just having fun here, till the OP explains that fascinating question more fully!!