I own, jointly with others, a 3 mile long road.
If there could be only two things that I impressed upon someone, in relation to this road, they would be the following:
1) You have no idea how costly maintaining a road (any road) is. I didn't. I had no idea. Whatever libertarian fantasies you may harbor about private people coming together to create and maintain anything like first world infrastructure, I am sorry to dash them: we have a group of 20 or so rich, well-educated, smart and hard-working people and it's right at the edge of our capabilities to keep this 3 mile long road in semi-acceptable condition.
2) The difference between doing a safe, reasonable, environmentally responsible and long term fix and doing that very same fix but 100% by the book is a cost difference of 3x to 4x. There are minor drainage fixes we've looked into that required, no shit, the army corps of engineers to be consulted along with several other county and state regulatory and environmental agencies. After paying a third party firm to create an environmental impact report. Do you understand that I am talking about fixing a ditch ? The army corps of engineers.
I did not, above, refer to "excessive regulation" because I am not ready nor willing to define that and I don't want to take a political stand on it - I am merely pointing out that the first thought you should be having on this issue is: regulations.