Not to keep on derailing this thread, but I bedroll my sleeping pad and sleeping bag in my bivy and strap onto the outside of the pack and I just call it my bedroll. Who cares what it's called , it keeps me warm n cozy n dry <3
I sleep by train yardz a lot obvi. Otherwise in trees by bike paths or walking trails, random patches of trees that don't have evidence of other recent bums. I usually try to get far away from the downtown of cities at night if possible. But yeah in smaller places, I just end up wherever under the stars! So easy to find quiet, chill places to camp in smaller towns. And in Australia, I sleep on the beach a lot.
In rain... on top of sheltered picnic tables in parks, in doorways of community center type buildings, overhangs behind late-opening industry or businesses (check google maps for hours lol), in abandoned rail cars, etc etc just get creative with whatevers around