I see that you're also presenting one single case known to you; this is effectively meaningless, and you know it.
The example I bough up may be anecdotal but It wasn't mean to show that people can get out of homelessness if they mess up and end there but rather to underline my argument that homelessness in general is only an "option" for a very niche type of person. There are also way way less female homeless people and it certainly isn't because females are somehow more capable to avoid total failure.
The person I worked with was homeless due to his family abandoning him (they where part of a religious sect) before he ever had the chance to stand on his own feet. But he was not the type of person that would accept homelessness and that's the sole reason he isn't anymore.
In the end people are scared to fall really low by trying to go high but while you indeed fall longer and further down when you fall from high you dont really end up lower. It just hurts more especially if you worked very hard to get up. With the exception of age/metal decline and health problems you very very likely get back up higher than where you started no matter what causes you to fail.
Well this is just not true. You have a fantasy view of life that does not ally with reality.