To further your analogy, would you prefer to be a diabetic paraplegic in the modern era, or the medieval? Because you're not going to be able to medicate yourself with the insulin you need, and there's not much work for paraplegics to do if they're not born into money.
> Our 60 years of wage slavery in windowless offices might seem unconscionable to a medieval peasant drinking mead all day by a stream with his friends, even if he ends up dying at 50.
We have the opportunity to change our lives if we don't want the wage slavery; entrepreneurialism is the whole reason why this site exists. For a medieval peasant, they can't move into the nobility, their inventions are not protected, they frequently aren't allowed to move around, travel is dangerous, communication with anyone outside the area they grew up in is more difficult due to language differences, hobbies are limited largely to what you can build yourself, since trade for items is difficult and expensive... the list of restrictions goes on and on.
In any case, the peasants of yesteryear are analogous to the working class of today, and they don't work in offices, windowless or otherwise.