Yes, of course. After prearranging with the landowner, you can do what you want. There are also some land use laws, but if you're out in the country, they aren't typically in place except in very repressive locations. In my part of the country, if I have 10 acres in the country, I'm free to build my own airport.
What does he do? I don't really care, I think he just shuts up about it and goes back to making the videos he likes to make. The point isn't really whether or not he wins. It's that he did what a safe, judicious pilot is taught to do and he was held to have violated rules because he exercised caution. If he had exercised disregard for safety, the lawyers would have been left without a case. For the rest of us, it's that we might be held to that same standard because a lawyer somewhere doesn't understand aviation. This isn't that different than the Warbirds case...a legal decision is setting a precedent which degrades safety.