I can't remember who it was but someone on this site who stealth camped a lot stated that, in small towns, he usually goes to the fire hall and asks if he can set up his tent on the grass behind them. They almost always are very interested in his method of traveling and are more than happy to accommodate him. They even fed him breakfast on one occasion.
He has also tracked down a local patrol car and asked if there was somewhere that he could sleep, again in small towns. Often they take him to a grassy area behind the police station or the local park/baseball field and tell him to set up on the edge out of the way. They often tell him that now that they know that he is there they will pass by during the night to make sure that he is OK.
I've done lots of this for years with my station wagon while at university. Do road trips to Canada and Mexico with parking in out of way lots and crawling into back for snooze.Back in the '70's, I did a 10k mile loop around the US in my Saab. All of my camping was 'stealth' - usually I just pulled the car off a small road, threw down a ground cloth and unrolled my sleeping bag. I slept next to the car. Sometimes I parked in deserted parking lots and did the same (add a foam pad). The car held all my food and a camping stove...I was not into campfires.
Yes, I did worry about my safety, but I tried to find out of the way spaces or public areas where the worst I could expect would be a LEO telling me to leave.
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I raced collegiate cycling and would pull up near course somewhere night before. Then meet up with people from other teams for dinner and pub. Afterwards crawl in back for the night. Best part was no rushing to race in morning since I was already there! <snip>