What can also happen is a lot of expenses and headaches in the form of repairs, taxes, cleaning services and property management for the airbnb rental (you'll need someone to clean it up, check it, handle the check ins), work you have to do when you go there that is taken from your skiing time.
Of course you don't know what property prices will do, but they might be highly correlated to how much people feel rich in the bay area due to the current tech boom.
All in all it *might* work if you really want it to, but perhaps you should consider that 60.000 in your stash is about 2400 per year "theoretical" withdrawal power at the start, plus 1000 (500?) per month from what you "would" have spent on the mortgage after the airbnb income/expenses/taxes. If you manage to spend less than that per year in skiing you win big, with increased full safety! ("no/little snow year? no problem.", "repairs? what repairs?", "financial crisis? cut 50% on the skiing for two years, no impact on income, no debt to service")
So personally I would say "no". But then again, it's your choice in the end.