If I had that sort of money, I would absolutely have a house in a place like that. Now, probably not JH because if I had that sort of money the last place I'd want a house would be next to other people (especially people who have that sort of money.) There are a lot of beautiful and mostly empty mountains in the rockies, both US and Canada. Though I think I'd get a lot more use out of the place by having friends and family use it when I wasn't... and I'd probably spend the $20m on a lot of land and a small cabin, instead of a big house and a small bit of land.
In the grand scheme of things, the ridiculous money paid for these places and their upkeep goes to support a whole community, and it keeps one of the most beautiful places in the US well funded to make sure it stays beautiful. Property tax will pay for a lot of park rangers, cleanup crew, search and rescue, conservation efforts, enforcement, etc. Club dues will make sure ski areas stay nice enough that people don't start expanding out and fucking up the rest of the mountain. HOAs will ensure not too many people are able to build houses and roads, especially in the mountains.
I find the Fed's speeches in Jackson Hole a very interesting phenomenon - it takes the city-dwellers who are at the absolute top of the game, and brings them out into the mountains for some small-town charm. A reminder of the better things in life, and life outside of concrete. Very USA, you know?
Got any photos, No Name Guy?