>>2424751The one thing that matters most is local weather. In US cities weather is the final say in if sleeping outside is a diminishing return. Where I am (Ausfag) you would be hard pressed to reach any less than -10c max.
This lead to a very minimal setup. Sleeping pag would be augmented with cardboard. I'd get what I could and stash. Cities always have food. Always. If you want to go scum mode you can just walk past dining outdoor settings as people go to leave and clean up what's left. If people see you doing it they might even offer you some food instead. It really depends on you and how low you are willing to be comfortable with.
One thing I always say is have no vices. It helps. A lot. Better to get some bypass tools for basic doors like pic related. I wish I had more pics of the actual sleeping spots behind most of these but at the time I was just absent mindedly more interested in pics of the places I slept and not gear or setups.
It's crazy how easy it is to hide in a city. You just have to be willing to walk past a lot of warning signs. Nowadays I am mostly out via tarp and hammock. Military bag, the usual stuff. There's a fine line between urban exploration and urban naptime.
The main take away is
Have a way to sleep temperature apropriate. Have clothes you can adjust or maintain, also temp apropriate. If you take a large bag you can go for a pretty long time just on packed food. For me I like abandoned stuff and sneaking into places. So that was the actual goal and I still partake every so often when I can. Just now I have all the shit I wished I had back then or didn't think to get into the habit of bringing. (Sewing kit for longer term, better socks, nicer flashlight etc)
Some poeple ignore the best option in the world. Pack a bag with the basics and just walk. Don't drive, get dropped off or take a bus, Just give yourself a month sometime and go walk. Walk till you have no choice but to stop. Or hide. That's all there is to it.