My driveway - all on my own property - is 5,300 feet from major highway to my home. It's all gravel, up and down a few respectable hills, has some curves to boot - and is mostly in a forest where ice doesn't melt too quickly. I built it in 1994 for a weekend place, then built my permanent retirement home in 2001. Power and phone are three feet under the road all the way in... The co-op's idea, not my request. But that works for me.
I have had no problems with insurance at all. They know of the road, and I have a pond near the house which is good for a hydrant equivalent. Since I have over 100 acres, I could not get normal bank mortgage anyway. They will not finance anything they can't sell - and they didn't care about the road. So I financed with Farm Credit. They did it easily, promptly and at a reasonable rate.
As for having to be rich to afford a long drive... I'm sure being rich would help, but I get by with only a modest income. With a tractor and box blade, I can smooth out the road regularly, and make gravel last a long time. I add a few loads of gravel every 2 to 3 years - although I went 4 years during the long drought several years back.
I value the privacy of being a half mile from any neighbor. I have dogs and other resources for security, and very few unwanted visitors. It's a great way to live.