The only time I was ever homeless (about forty days, well over a decade ago) I slept between beaches and couches, and quickly discovered that having one's own secure space is essential to healthy living.
Although I was worth less than nothing (i.e. negative money from CC/student loans), these are among my happiest days. Once I found employment as a nanny/driver I was allowed to sleep in the servant's quarters — and eventually built my own room in an unused garage.
Definitely having a family to feed, in addition to one's self, would make this kind of lifestyle impossible — but I fear as wealth inequality increases, and more people are living in multi-generational living arrangements: family entrapment (both caring for children and parents) will increasingly be how destitute get by [taking care of them].
I will never be homeless again. Just an awful existence.