No one ever does everything right. But some people have enough money, enough smarts, enough social capital, etc. that it gets mitigated.
We should be seeking to make sure more people have access to mitigation rather than looking for the one mistake someone made that somehow makes it okay in our eyes that they have gone from having over a million dollars in inventory to couch surfing with friends and relatives as the only reason they aren't on the street. And if their social network runs out of forbearance, the street could be the next step.
I'm not arguing he's some paragon of virtue who got screwed. I'm arguing that no one should be expected to be a paragon of virtue to have any hope of making their life work.
Paragons of virtue should see terrific outcomes, not merely "Oh, you get to not be homeless today. Go, you!"
Anyway, it's 3am. I think I shall stop here as I'm not clear more words will make anything clearer beyond this.