There were times that the Romans auctioned off the right to tax a region. So you’d pay the state some sum and then have the right to extract whatever you can from the population.

I’m sure the whole story is much more nuanced than that outline.

This is how parking enforcement works in some major cities (e.g. Chicago).

And I thought debt collection agencies are shit. We really do live in the best times so far.

Even 18th century pre-revolutionary France did this sort of thing. The great chemist Lavoisier was executed by revolutionaries, not because he was a chemist, but because he was also an administrator of the ferme générale, the privatized tax system of the time.

You said taxes for the different markets (such as luxury goods, Granary, and imports) all of the citizen shop at, and then you set separate real estate taxes for the patricians which are the wealthiest class in the society. And you can see the little dude walk around and get the taxes. The game really holds up, it's my fav =)