Another trope is "the only alternative to the current state of affairs is the worse possible thing I can imagine".
This isn't even malicious, it's just an expression of the person's fears.
Practically, surface streets would likely be owned and managed by a corporation, whose shares are owned by the people who live in and operate businesses in the vicinity. And you wouldn't move there without doing diligence on the situation.
This is exactly the situation in many communities where the streets are owned by the homeowners association. Also happens in rural areas where several houses are served by a street that connects to a city road. The maintenance of which is paid for by the home owners in a way they agree to.
Contracts to manage things where property is owned by groups of people exists in the current system can can be applied to many situations that are currently handled by the government.
So the same situation as now just without the democracy.
And no legal protection from monopolizing those resources.
>Another trope is "the only alternative to the current state of affairs is the worse possible thing I can imagine".
On the contrary there are many ways to improve the current state of affairs namely more restriction on abusive behaviors not less.
And indeed there are many ways to make things worse. The kind of lunacy I pointed out is firmly in that category.
So no, practically speaking, the profit to be had from acquiring a monopoly on streets in front homes and business would be so great that, unless there were non-salable restrictions on the practice, those resources would quickly be bought at irresistibly high prices to create an absurdly profitable monopoly.
If those city assets came up for sale right now, any sensible investor would buy as many roads as possible in every town possible and charge the highest rate possible. If it were all under a single company, all the more profitable.
Indeed, the very last person who could ever afford to buy city streets on the free market would be a small business or home owner.
Imagine yourself describing a democratic republic to people that have never heard of one. Now imagine that every one of them, down to the last man, suggests that your system will inevitably result in a zombie apocalypse that destroys every living thing on the planet. Also imagine that certain oddly specific details, such as the color and consistency of the zombie blood, is common across all people you talk to.
That is what libertarians experience whenever they describe libertarianism to non-libertarians. It always ends up with people starving in the streets that don't exist because no one built them.
Your scenario, in which one person buys all the streets and then prevents everyone else from using them at reasonable cost ends with that guy getting his head caved in with a chunk of asphalt dug out of one of his own streets. Rule number one for any civilization, regardless of its form of governance, is to not be an asshole. The release valve for people abusing the system is other people ignoring the system.
If you antagonize everyone, then no one will help you police your many miles of streets, to make sure no one on them has not paid. You have one cop car, but no one pulls over when you flash the lights, and if you try to issue a ticket, people crumple it up and throw it in your face.
This is completely independent of the laws or governance. If you don't help other people, they eventually stop helping you. If you coerce other people by force, eventually they start fighting back.
In reality, most people are not jerks, and road investors will likely find that they could have lost less money by buying a boat. The only profitable roads would be in the commercial districts and the highways, and those would probably make more money on parking, advertising, and rest stops than they ever could from direct charges to businesses and the public. Sensible investors would avoid them like the plague unless they already owned some sort of business related to them. Your city roads will be maintained by McDonald's and Wal-Mart, and your highways by ExxonMobil and Chevron. Major bridges and other large capital investments would have associated tolls.
This isn't even malicious, it's just an expression of the person's fears.
Practically, surface streets would likely be owned and managed by a corporation, whose shares are owned by the people who live in and operate businesses in the vicinity. And you wouldn't move there without doing diligence on the situation.
This is exactly the situation in many communities where the streets are owned by the homeowners association. Also happens in rural areas where several houses are served by a street that connects to a city road. The maintenance of which is paid for by the home owners in a way they agree to.
Contracts to manage things where property is owned by groups of people exists in the current system can can be applied to many situations that are currently handled by the government.