I'm going to try to make natural paths in my second town, but man. What a pain in the butt to maintain.
If you put down pattern paths for a while and follow them they start to create a natural path underneath and then you can pull up the pattern for the natural look, it also helps to block it off with something, like making the boarders of the path you want to obtain and then run in between the boarders, it doesn't make it easier to maintain, but easier to go over the same place everyday.