We seldom get snow but some thoughts from my experience. I have two old neighbors I do some favors for as they need them and enjoy it greatly. They are quick to say thank you even if I do something they were not expecting. Here that is removing dead trees stumps, cutting a yard or leveling dirt. Not the same as moving snow. Then I have a brand new neighbor who needed some dirt moved and was doing so with a brand new wheel barrow and it came up why his contractor did not do it with his fel and the subject of damaging concert came up. I did not feel comfortable with the tight area it was so never mentioned I could do it for him in 5 minutes and would be glad to but not for how tight camper was parked and so forth. Now if they expected it on regular basis nope.
Then other site is there is an "easement" across our property to three landowners behind us. Dirt road, we own the land and pay the taxes on it but no value to us. I did scrape it when I first got blade that would and did so till one day the county's road plow did the road, maybe two months later they did again. I called and asked and was told it is because of liability we must for we did scrape it years ago. (They had not for years when they began back.) I said liability? I was told if anyone wrecked due to anything related to the easement's condition they were liable so I was very glad they took it over. They just scraped it today.
But a question on private road, is there no owner to them? We have them here also but is there not a real owner for that land the road is on? Had never thought of that until reading this. But it is my understanding there is here and now what kind of liability the owner has have no idea and am sure it would vary from state to state.
As insurance agent if you are charging some for working on the work you are taking on a risk as a commercial business. Even if you have great relationships with everyone on the road you do not with all who visit them. Be a friend but know your full risks.