The challenge, as always, is to never underestimate a bubble's capacity to outlast your solvency. I personally know people who have been heading against the housing "bubble" in Canada bursting since 1999. They've spent a lot of money with nothing to show for it, yet, and missed out on housing prices, like, quadrupling? Quintupling?

So, good luck. Buying out-of-market puts might be a safer bet, since you're most likely to "just" lose all your money, with a small chance of a massive payout of it "properly" crashes.