Rich buyers historically propped up Aspen's housing prices even when the U.S. economy tanked, but even they couldn't protect the local market from the Great Recession and the recent housing bust. "We learned in 2008 and 2009 that we're not immune to broad economic cycles," Ernemann says. So buyers looking for the best prices in ski country should obviously hunt for deals when the housing market and broad economy are weak -- as they still somewhat are today. The time of year when you look for ski properties can also make a big difference. For instance, Ernemann says Aspen's bargain hunters often wait until just past the community's key February/March and July/August home-buying seasons and focus on properties that didn't sell.