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.
Private roads are actually pretty common, found in older suburban development and in rural areas. I live off of one that is about 300m long.
They are unpopular since they effectively require a very small private association to maintain them. They really hurt property values (one reason I bought my place at a bargain price). Most jurisdictions try to prevent creating them because they lead to disputes between neighbours, or poorly maintained private roads become a problem when an emergency vehicle needs to get down one.
The budget for local roads is also quite small, since they don’t carry much truck traffic. My township of 5,000 people or so has 3 part time guys who maintain the roads and a few pickup trucks and a dump truck for hauling the asphalt. That’s it.
The most expensive part of road maintenance is replacing bridges.
The second that road gets defunded by the public coffers, guy with tractor would show back up.