A good comparison would be the “Robber Barons” on the Rhine River in centuries past, who would place barricades across the river to block any traffic until each vessel paid tolls. And there were dozens of such petty nobles doing this, each with their separate barricade. It eventually got so bad that the Rhine stopped being a viable route for shipping. That is what happens when there are too many unregulated fingers in a single pie.
In short, we don’t want lots of small road-owners each placing their own fees such that we have to pay a hundred charges in order to cross the country. Instead, we would want nation-spanning “Road Corporations”, akin to rail or air travel, where you could cross the continent on a single company’s system, while having the choice between a few competing systems for reaching most major destinations. Of course, that brings on the same sort of regulatory issues that apply to railroads.