Excellent perspective Steve. I think you are hitting the nail on the head.
Our pioneer ancestors worked so hard to buy their freedom, and were glad with the equation, that the more they did for themselves, the less they were beholden to money lenders and the lords of the manors. That may ring a bell for those living the present day dream.
Common people today aren't really in a much different situation than in Roman times. Mostly we are born slaves. That's been the natural order of complex societies, the majority are given no wriggle room but to produce for the masters. But even the Romans allowed any slave to buy his freedom, if he could ever get the cash together. I am sure that just like in the present culture, they offered all sorts of distractions and pitfalls so that most never were free men. And even if you bought your freedom, then you had to house and feed yourself. I can imagine that many paid a high price, only to later sell themselves back into slavery. But the prospect and reports of one in a thousand becoming free probably prevented many an insurrection. Sounds familiar...
To me it seems that the American dream, or from my perspective, the North American dream, was a unique historical event. Over centuries a new frontier opened up, where property wasn't the critical factor for success, individual strengths of arm and brain were. People began to think themselves equal. They rejected lordship and title. Our democracies and social networks guarding against the powers of inheritance and the rich grew from that, and made North America the greatest power ever. No accident, as the rich have never distinguished themselves for great use of resources.
And now it is evaporating into peerage, corruption, silver spoons, and a culture of indebtedness.
The only way out of that I see is from the work of one's own hands. Yes, it will always be more work than to give money to the oligarch for the thing he arranged to have made with heavy machinery, government subsidies and slave labour in China, Indonesia, or Bangladesh. But the money you don't have to spend means less money in a secret Swiss bank account, and less power to people who share nothing at all in common with the interest of you and your family.
To me that is the only option for freedom on a slanted playing field. A world made by hand. Why Ghandi spun thread on a hand wheel, or walked to the sea to gather salt when the British said it was illegal.