Can street cleaners evolve in a free market?

I don’t think you are looking at government-free cities at the right scale. It makes a lot more sense for cities to scale up than for governments to. A large metropolitan area needs “streets” (infrastructure) that span over hundreds of kilometers.

But if the city is not a judge in disputes involving itself, and there are multiple such competing judges in this city, then this city is no different from any multi-national corporation. Just like Sony is staffed by citizens of many nations, and operates in many nations, so can a city.

Like Snowflake said, this initial scenario is already impractical and typically only made possible through government intervention, for exactly the same reasons that you’re trying to denounce the free market.

The only real “higher power” that would do such an idiotic thing is a government.

How can we pretend to know that? Only government and mickanomics ascribe omniscience to themselves. Any of the following could happen: all of the residents chip in because it’s that beneficial to all of them; some of the residents chip in because it’s that beneficial to them (even without the cooperation of the rest); one resident pays for it all because it’s that beneficial to him; a private company comes in and builds the road then charges a toll; a private company comes in, builds the road, and then only paves driveways up to those properties that pay a due; all or most of the residents are members of a HOA or similar organization and regularly pay dues, so the HOA takes the responsibility of creating and maintaining the road; something not listed here that a clever entrepreneur came up with, because entrepreneurs are always coming up with business models and solutions that others can’t even fathom.

Let me call these hypothetical people and see. Seriously, does it matter? If big trucks can’t drive down their road, tough shit, because it’s theirs. They can find another, or the owners of the road might realize that they’re losing a bunch of business because of such a restriction.

Probably horribly, and rightly so. Even under government, nobody gets roads “for free.” The cost is just spread evenly across everyone in the form of taxes and inflation. It’s possible, as demonstrated by some possible solutions that I listed above, that they wouldn’t even get access to the road without paying. If you think it’s more just for everyone to pay for all roads, regardless of their usage, as opposed to the users and beneficiaries of a road paying for its upkeep, then we shouldn’t even bother having this discussion, because you’ve already made up your mind.

Out of all the answers I’ve heard in this most recent episode on this thread, snowflake’s observation that the problems are “solved” through common landlords and contracts rings the most true. However I believe that common landlords and contracts have almost the exact set of problems (in the long term) as governments for reasons discussed much earlier in this thread. So to save us all from going round in circles I shall make this my last comment in this thread unless someone posts something here which covers genuinely new territory.

Rather than taking our word for it and cherry picking which response sounds most pleasing to your ear why not read up on the subject? 22 pages on this thread you were willing to invest time into, why not invest time into a good book instead?