I did this in Toronto and SF for a few summers in my 30s, well into my "real life" and beyond college. It was transformative, like creating my own UBI. Found all the same benefits: mundane daily moments become magical. Unexpected hospitality of strangers when I [on rare occasion] needed it. Admiration of friends and strangers. Etc etc

The main thing I did different was using a hammock tent (10min setup, 10min teardown each day). So I stayed in very public places (right off major foot traffic routes) and just went to bed early and got up at sunrise.

Also, I told everyone. No authority cared that i was doing it. In fact, i was organizing weekly events for government employees (some quite high level), and they all thought it was hilarious and were supportive.

Here's my learnings: https://github.com/patcon/urban-camping

EDIT: Ah, and these were my notes from living in rented shipping containers with a friend: https://github.com/patcon/container-city/wiki/Notes