I think Windham may have a shot at the private club thing…..maybe. It’s close enough to a massive population hub and with what Hunter has evolved into there may be enough demand for this kind of experience.
Someone mentioned that people with big money fly out west or to Europe to ski but not everyone wants or likes to fly. Covid has made a lot of people Leary of flying too. Being able to drive two hours for a weekend getaway with an uncrowded and more posh ski experience might actually work.
As far as being flat I bet there’s plenty of skiers with money in the tri-state region that don’t care about that at all, even if they claim otherwise.