This was a choice (essentially to save money) and the author had multiple fallback plans. Real homelessness is born out of desperation and lack of alternatives. Tragedies of mental health issues, abuse, severe financial distress, no savings, debt, warrants. No nice shower at the gym, no locker to keep a laptop and two suits. The constant fear of not just the police but also of getting robbed by another homeless, likely after something to sell for drugs. That's very different from anytime being able to crash on somebody's sofa to save on rent so you can earlier "afford to build companies".
We can even see it in one of the later paragraphs where potential spots in the bay area are evaluated. The local homeless should not be close. Oh, they shouldn't? That gives you an idea of the conditions actual homeless folks need to live under.
Here's an unintentionally hilarious meta-post on the subject https://news.ycombinator.com/item?id=29531915
First hit on Zillow: https://www.zillow.com/homedetails/4207-Marina-View-Way-Cort...
$1.9 million for a 3 bedroom, 3 bath, 1600 sqft.
This seems like... a bad plan if your goal is to run a website whose primary purpose is not entirely legal.
How are they measuring this?
What an incredibly simple idea. Just scale it up.
You've been handed a golden opportunity to set the right course.