I was very much with you until this sentence.
I think if you ever conclude that someone deserves a bad fate, it's because you haven't looked hard enough to find a reason why they don't have a better fate.
Maybe they were born into homelessness. Maybe they missed valueable educational opportunities as a child. Maybe they were prescribed opioids, and developed an addiction. Maybe they suffered a string of tragedies that robbed them of their optimism that they could have something better. If it's not one of those, I guarantee it's something else.
There is, in fact, no branching off point where you can blame a person's fate on themselves, rather than their circumstances. It’s always the circumstances.