In my experience homelessness is a great way to teach a person what they actually need to spend money on and just how much they don't need. Whether it breaks a person or they come out stronger does seem to depend on the person and their principles, for sure, so I'm not advocating throwing everyone under a bridge for a year (this isn't Sparta...). But you're definitely confirming my experience and takeaways there :-).
Homeless in Chicago seems like it'd feel dystopian. Heck, walking around much of Chicago outside feels dystopian, from the giant buildings that feel entirely uninviting to the boarded or barred up windows/doors at street level (which do turn out to have some nice bustling restaurants and other businesses inside). I haven't spent a ton of time there but it did not feel comfortable while I was. I'm sure it's a bit different when it's where you're from, but gotta say Cambridge definitely felt like a nicer place to sleep under a tree.