Interesting question. I have kind of an odd ball suggestion...Deadwood or Lead SD in the Black Hills. These towns are a few miles from Terry Peak and Deer Mountain which aren't the greatest ski hills on the planet but get a fair amount of decent snow. I remember an early bird season pass was like 200 bucks at Terry Peak in my college days ten years ago. I would compare them to the resorts of the northeast with way better snow. South Dakota is dirt cheap, has no state income tax, and the black hills are actually a super cool area in any season (Google Custer State Park, Needles Highway, Spearfish Canyon, Badlands, Jewel Cave, Wind Cave, Sylvan Lake, Lake Pactola, Deadwood, etc. etc.). If you buy a cheap house in one of these towns you can rent out your house for crazy sums of money to the more wealthy folks that attend the Sturgis Motorcycle rally(get references, you are in demand as a home owner and can get very courteous renters) about 20 miles away, and then take a paid for vacation(you will want to leave during the rally). You are about 30 minutes from Rapid City which has every consumer comfort one would need at roughly 80,000 people.
In addition to the perks of being in this immediate area you can get to some really good big time resorts in 6 to 8 hours including Steamboat Springs, Jackson, and Big Sky (personal favorite). I am biased being from South Dakota, but man for living a good life the Black Hills are hard to beat.