Do you understand why this isn't a workable solution for everyone, and likely not even for the last 10% of your journey?

It would work beautifully for the last 10% of my journey. The only reason why there are no private roads for the las 10% is the county tax funds that road, and only a complete and utter moron would build a road when their "competitor" has a price of zero at the point of use. People commonly ask why the public road has a monopoly; it's not that they are a natural monopoly but rather that it's literally impossible to compete with someone with zero costs (tax costs already sunk) so places with public roads have ~no competition.

The second that road gets defunded by the public coffers, guy with tractor would show back up.