Private roads are very, very difficult to build in modern America. The biggest issue is that people traveling on a private road are not allowed by the government to sign away their right to sue, and the liability for the private road operator is enormous.
Other issues are the thicket of regional planning regulations. There's really not truly private property any more, roadbuilding of any type is subject to the state and local political process.
I'm afraid you're confusing a symptom (the over-complexity of our society) with a cause. My advice : read the always fresh and mind-blowing Joseph A. Tainter's "Collapse of complex societies".
Other issues are the thicket of regional planning regulations. There's really not truly private property any more, roadbuilding of any type is subject to the state and local political process.