If I was rich rich I'd definitely shop for a place at Yellowstone. Mainly because its attached to Big Sky. Greg Lemond has an awesome Adirondack camp like setup there I saw on some sort of Lifestyles of the Rich and Famous show. Nice. That was a weird bankruptcy that only rich people gathered into a club can pull off. Moonlight went under because it was essentially a Lehman owned venture, and we all know what happened to Lehman.
To add some detail -
Yellowstone went bankrupt due to the developers Tim and Edra Blixseth borrowing $375 million in 2006 from Credit Suisse (it was questionable why Credit Suisse did the loan as they did zero due diligence) using the Yellowstone Club as collateral and
keeping $209 million as a dividend for themselves. This directly led to the bankruptcy. The current owner of the Yellowstone Club is Cross Harbor Partners (which includes members of the Yellowstone Club). Yellowstone Club as been operating ever since it was purchased by Cross Harbor.
Spanish Peaks went under due to the financial mess that started in 2008. Spanish Peaks was bought by Cross Harbor and Boyne Resorts and integrated into Big Sky.
Moonlight Basin's primary lender was Lehman and when Lehmen went under so did Moonlight Basin. Cross Harbor and Boyne also bought Moonlight Basin and integrated it into Big Sky.
At The Hermitage in Vermont (former Haystack Ski area), Jim Barnes bought then named Haystack Club in 2011. He then went on a borrowing and building spree that included construction that lacked permits. He could not make the payments and was foreclosed on by the bank, VT came after him for non-payment of taxes and he faced lawsuits for fraud after taking $2 million for townhouses that were never built.
Members of The Hermitage bought out the assets and are now operating the club.
The one common thread is that the first three examples were all started from scratch. Another common thread is the shady behavior by the developers. Also, in this time frame, is the mess from the 2008 financial crisis.
Windham is a completely whole, successfully operating ski area. The current owners had access to all the financial numbers, not made up numbers based on projections. It would be very easy to financially make the decision to convert Windham to a public/private club and make it profitable. There are at least 2 decent size ski area examples of a pubic/private set-up in NYS: Holimont Ski Club right next to Holiday Valley and Hunt Hollow Ski Club in Naples, NY.