Most HN posters in the U.S. probably haven't experienced true financial stress. It's toxic. It makes you paranoid. Benzos don't help (and they're a terrible long-term solution anyway). You have a constant cold because your immune system is shot. And you never get used to it. It never gets better. The cognitive load is both intense and purely negative. There is no good in it. People who romanticize "poverty" are usually talking about something like grad student life (little money, little expense). Financial stress is as poisonous as ingesting paint thinner, and even a few weeks of it can permanently fuck someone up.
I think that most homeless people have severe mental illness that is not their fault (and that deserves compassion and treatment, not stigma or abuse). If they didn't have it beforehand, they'll have it after a few months of that life.
I think it's damn heroic that Leo was able to summon the cognitive clarity, after that kind of long-term damage, to build something. Unfortunately, that's not going to be enough to get him anywhere near the level of mental health that would enable him to hold down a typical white-collar job. That's a fucking long road.