Our current road system was designed a long time ago and the current way of maintaining them for the purpose they provide is how it must be. We are not talking about foot roads but roads to handle man made automobiles, trucks and other equipment. The idea that roads should be privatized is absolute ignorance. Why would I pay to drive your road when I have a right to egress/ingress and can just sue for passage across your property since by your vision everyone would be land locked? And that is just one of the many problems with your idea.
This post just proves to me that anarchists have a screw loose. You cannot begin an anarchist society unless you start from square one and that ain't gonna happen. Everyone "benefits" from our infrastructure and since we are not going to tear it all down and start from scratch then it is what it is.
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