I wasn't completely broke but I couldn't keep affording rent as expensive as it was. I was able to shower at a gym, and worked out of Tech Shop on what I was trying to build. But it's hard -- like super hard to just be homeless. The social stigma associated with the word alone is hard for people to get beyond. I would often hear, "But you don't seem like the type to be homeless" and then they would slowly just distance themselves from talking to me. Super weird.
I have been harassed by cops, you feel extremely transient and embarrassed just to be alive at times. Sleeping in a van sucks too. Street noises keep you up, cramped for space, etc. On the up side there is a contingent of tech people that are doing the same thing, so I had the pleasure of meeting some others like myself.
I've never taken up the opportunity of food, shelter, or clothing offered by the city, because frankly I'm doing this on my own accord, so I can't speak to how that part of the system helps people get back on their feet.
After this entire experience my heart breaks every time I see a fellow human having to resort to sleeping in the cold, wet, outdoors with no shelter and nothing but some cardboard and discarded newspapers to cover up with. I often wonder how close I could have come to being completely broken by this decision, and what coincidences led someone down this path. In the end it has helped me understand that we must all care more for one another, no matter what.