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But in the US the average consumer doesn't have a meaningful choice between road companies: http://arstechnica.com/business/2014/09/most-of-the-us-has-n...

This is the heart of it. Free market economics is a wonderful thing and as a civilization we have reaped enormous rewards from it, I'm a true believer, but if your market produces natural monopolies that are highly stable then that's not really a market anymore and it's certainly not free or fair.

Adam Smith, the father of free market economics, was very clear about this. Markets must be well regulated in order to remain free and fair.

thats not devil's advocate as much as it is a "racketeering advocate" [1].

[1] Racketeering, often associated with organized crime, is the act of offering of a dishonest service (a "racket") to solve a problem that wouldn't otherwise exist without the enterprise offering the service.

And because roads are expensive, there is only one. If you don't like it you just have to fly your helicopter to McDonalds instead. The market works!