Now this is going to sound like a hot take, but have people ever considered that the existing homeless population is itself a real life ongoing case study/experiment in this not being possible unless you're like especially lucky? Or the fact that the vast majority of youtubers do not make a million dollars even over several years despite now having several years of experience in youtubing?

It's not like homeless people are choosing to stay homeless because they're secretly practicing streetmaxxing or being on that hated-by-bougie-society grindset, they're legit unable to turn things around; this isn't a TV show where a homeless person makes the choice to give up drugs, then turns his life around and comes back to that lady who was always supportive of him dressed in a suit now that he's committed himself to turning his life around.