one of the most privileged people of the time

I don't think his level of privilege has much bearing on the approximate accuracy of the numbers he cites, which are what is relevant to my argument. I don't think he was making that stuff up.

would you have rather been an average person from say, 0 BC to 1800? If so, where/when?

No, my own life has gone well enough, I got what I wanted. What I'm advocating for isn't anything I need for myself. But when I talk or read the accounts of people who feel financially trapped, particularly young people, there isn't any realistic advice to offer. What worked out for me isn't reproducible and isn't available to them. I don't have a deep enough knowledge of history to talk about specific times and places. But for someone who resents the life that has been chosen for them and doesn't want it, sure, why wouldn't they be better off rolling the dice with historical circumstances? The specific malaise affecting them now was not there, and maybe whatever hardships would be faced instead would be more tolerable to them. But there's no reason that should be the standard anyway. We are so rich in resources compared to any other time, there is no justification for anyone to be trapped like that. Everyone can be free to do what they want, and so they should.

I think I have said all I have to say on this. It bothers me that you seem to think it's acceptable to let people who find their work intolerable to fall into despair and kill themselves, but you've made some valid arguments and it's refreshing to discuss this with someone who does not seem to be a property rights absolutist, so thanks for sharing your perspective.

Edit: One last thing I want to mention, beyond making a point about whether the progress of civilization is a strict improvement, Debt: The First 5000 Years is also a comprehensive critique of the moral logic of debt. If it seems strange to reject that logic, I again recommend that book.