Time to bounce a reality check: a lot of companies let their employees go vultch in the individual market for health insurance. That might even have been a purpose of Obamacare: make labor more mobile by removing the need to stay with an employer that actually provides worthwhile health insurance. Even the typical company-supported (though not fully paid) health plans tend to be sketchy basic policies with some kind of catastrophic-loss backup. Obamacare & CA rules require that they offer health insurance; they don't require that it be worth much. At the place I'm working now, the company policy is pretty minimal. Luckily, I'm also on Medicare (due to age, not disability) so the total cash out isn't horrible.

As for paychecks from homelessness, I suspect that almost nobody making less than $250K is more than 6 or so. Mainly because most people do live paycheck-to-paycheck with little in the bank. I have more banked than most, and I could probably last a year and small change.

As for homeless encampments, I've seen many under highway and railroad bridges, and along railroad lines especially where they're under a freeway bridge. Perhaps those are popular spots because the bridge is big (nice roof), and ownership and policing is kind of a grey area. Occasionally something goes wrong and a fire happens. Can be nasty. UP lost a large chunk of the former SP American River bridge in Sacramento several years ago to a homeless-involved fire (and replaced it in less than 2 weeks).