The life stories you mention were fascinating, and inspiring, as they usually are with tales of endurance and determination. I've heard stories like that over the years, too.

However, there are millions of people in the US, and billions around the world, who work their guts out all their lives, for absolute crap - if they're lucky! Should they be content with their station in life, since they didn't show enough initiative and drive to get out of their poverty?

That view would be meritocracy gone mad, in my opinion. It wouldn't be taking the bigger (socio-economic) picture into account. Not everyone can be a 'winner' - society is simply not structured that way.

20 years ago I would have recommended J K Galbraith's books as primers on the topic .. unfortunately that was the last time I read any political economy, so I don't know what I'd think of them now. It might be time to revisit them