Any folks who grew up on a farm who can confirm?
I wasn't allowed to fell the trees but I had to use a chainsaw and cut the branches off the felled trees and then section the denuded trees into small enough rounds they were suitable for busting into firewood with an axe. I was given the option to learn to drive my grandfather's stick shift Toyota pickup truck in order to move all the wood with that, or move it by hand. It was an easy decision.
But, yes, until you're talking about more serious off-road/bad road (which is challenging in a completely different way), there's nothing especially hard about driving on a private dirt road.
Also driving the shitty back roads in Finland was a lot of fun in my old Honda Civic which didn't have power steering or ABS (let alone any kind of traction control and stabilization you have in newer cars). Driving a modern car with all the modern aids is very easy on dirt. On snow some of them can hinder you though (some automatic gearboxes just don't know what to do when none of the wheels have any traction) but for the most part it is very easy too if you have winter tires.
Driving is very easy. Too easy I think which causes people to drive way too fast for the situation quite often.
Main issue for driving on dirt roads/snow for automated cars I see is just seeing the road itself correctly not with controlling the car.