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And after 100 years of propaganda, we actually believe there never has been a better system.

If you mean the way a medieval village or town functioned, then this comparison omits the improvements of "capitalism" over it.

Person make chair, person sell chair, person eat - that's if they are this village's or town's chairmaker. If not, they are treated as if they stole from the chairmaker. Teeth kicked in, banished. Something like that. The chairmaker's role is transferred by inheritance or by apprenticeship from one person to one other person. Like a noble's title.

The way medical practice works in some countries with English law, I've heard, still reminisces that, and the results are not liked generally.

Choices and social mobility and social lifts are not present in a traditional society. That village remains in one place over many years. It may grow or shrink, but there's simply no need to allow cook's son to become a chairmaker, or vice versa. Or if there's is, the whole village may assemble and talk about such a decision once in 10-20 years. If he has two sons, then one of them works for the other, can't be cook on his own. If he wants to be his own man, he can try and find an apprenticeship, if some other master doesn't have a son or an apprentice. In other place maybe.

In a city it was similar, except, to scale the same "natural order", guilds existed and not small families, but guilds' heads would make such collegial decisions. Or heads of merchant families.

What you feel as oppression now is not really worse than what a medieval man felt, living all his life the same way in the same place.

I blame Marx for this misconception, he probably tried to play the "good old times" typical German card, but his followers, as a result, often believe that industrialization somehow made free people wage slaves. No. Try living in a village, today, in a western country. And then imagine you wouldn't work or travel elsewhere, all your life would be around that small place, with the same few people and families year after year. Social lifts and social mobility, vertical or even horizontal, were simply unimaginable in such a structure.