Used to do it when I was homeless, it's not really as fun as you'd think worrying about the pigs coming and telling you to move out and possibly citing you. I guess it would be different if you could go to an actual home when you're finished though.
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I did this like every night when I was hitching. I would mostly try to find secluded patches of woods where you would have to crawl through some bushes or something that would make it kind of hard to get into them. I would scout out the area earlier in the day then go in right as it was getting dark to set up my tent. I never slept in a roundabout but I did sleep in comparable places a few times, like in a patch of pine trees in the parking lot of a supermarket. Pine trees are nice because the needles on the ground are soft to sleep on.
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