If you buy now, your property probably isn't going to tank (unless it's just ridiculously overvalued for what it is, and some houses in SF certainly fall into that category). SF will be a hot market for a long time to come, thanks to its constrained inventory. But housing might not appreciate significantly over a 5-odd year horizon. Which is fine, fwiw, because one shouldn't be buying housing as an investment in the first place, much less as a short-term investment. Buy income-generating rental properties, with significantly better tax incentives to boot, if that's the goal. Buy a house because you want a place to live. If it happens to appreciate in real terms, and not just in theory, that's gravy. But over the long run, it's unlikely to do so, especially when you factor in all your maintenance, holding, and transaction costs.