It sounds like you are not aware of all the 'innovation' UK has explored in 16-18th century, where people had to pay for being in jail, were charged for being judged, we had debt prisons and people ran their business from them! Also we gave cocaine to kids when their teeth hurt.

These ideas are preposterous by modern standards, but people can and have come up with arrangements where a person works from jail without becoming a slave.

Can a 'free man' survive 'however he sees fit'?

You can't even walk around 'freely', some guy in Uk was trying to cross the country naked and spent 2 years in prison.

Build a house in the woods, plow the land, hunt without a license, and someone will show up to deal with you. Sing a song in the street? You are breaking copyright and some public nuisance or antisocial behaviour laws. You built something with your own hands and sold it? Might have broken some patents.

About the only thing a free man may do is work for a man freer than him. I appreciate we have a civilised society, but compared to free day of olde, it's a total straigh jacket.

So no, these situations are not equivalent but they are comparable enough that I don't buy the categorical moral judgement you are casting.