> if >90% of your work can be replaced by a machine
My point is that the amount of work in a warehouse that can be replaced by a machine - even with perfect robotics - is far less than 90%.
> The actual differentiating factor between people who climb the socioeconomic ladder and those who do not is grit (not intelligence).
You forgot an "f" in "grit". The notion that success is simply a matter of hard work is a fairy tale told to us by people who've worked far less for their immense wealth than the rest of us worked for our pittances, specifically to trick the working class into accepting a shit deal.
The reality - that the richer you are, the easier it is to become even richer - should be entirely unsurprising to anyone who understands positive feedback loops - or, for that matter, to anyone who's ever played Monopoly. Wealth buys power, and power enables extracting more wealth; rinse and repeat ad infinitum.
Put differently:
> The people who make them earn them, mostly through sheer hard work.
There is not a single billionaire on this Earth whose wealth came about "mostly through sheer hard work". The vast majority of that wealth comes from having already had some wealth, which they then invested to produce more wealth, and so on indefinitely. That wealth gets passed down to their descendants, the same way it was passed down to them.
The starting point for "wealthy enough to enter the passive income feedback loop" is land - one's home often being one's first major investment. From there, the path is rather tried and true: buy another house, rent out the old one, rinse and repeat until you can afford apartment complexes and commercial properties, rinse and repeat that forever. For anyone who ain't a complete imbecile, private land ownership is an infinite money cheat - one for which the rest of us are paying through the nose.
> Our main dysfunction seems to be propping up organizations that ought to fail, for fear of the temporary instability caused by their failure.
That propping up is a direct result of the positive feedback loop at play. More wealth → more political power → more wealth → more political power → ∞. Of course the socioeconomic system effectively under the direct control of the rich and powerful is going to primarily serve said rich and powerful at the expense of literally everyone else; bailing themselves out is in their vested interest.
Meanwhile, what's their message to the ever-growing working class getting the short end of the stick? "Work harder." "Pull yourself up by your bootstraps." "It's all about grit." "Don't listen to anyone saying that privilege matters." Hopefully you can see why your argument doesn't really resonate with people who have been applying increased grit and only getting back decreased pay relative to