You have a deep, implicit assumption of a social contract in your statement here:
> Since society is taking up the bulk of the work in helping you re-enter, you have to make some compromises, and potentially moving to a new place seems like a reasonable one to make. If we want a robust and strong social safety net, we cannot commit to providing all these services in the most expensive place to do so.
Some people can't. I know several schizophrenia sufferers who would never be able to hit an expected checklist. Some are brilliant. Some think they talk to an esoteric God and babble prophecy. None are functional.
We used to lock those folks up in sanitoriums for their safety, but due to systemic abuse this ended. Go back further, and the folks were tribal shamans, village jesters, and other elements of society which were supported by others until their (often untimely) deaths.
The latter support more or less ended when we as a species started settling down out of nomadic lives.
As a society, we dramatically underfund infrastructure (crumbling bridges and suburbs), healthcare (exploding costs without quality improvement), education (teachers salary is uncompetitive), government action (court systems aren't expedient, legislators xna be bought).
If we don't want these things, we should have the society decide so. This would be through legislation. But we haven't. We ignore these friction instead of addressing them.
Resolving friction takes effort, and effort has costs.