Or possibly worse if the market crashes again and now I’m stuck with two underwater properties, neither of which are where I’d like to live long-term.  

After the housing crash, my long time tenants moved out and I was moving off to grad school, and I could not sell my house (I was way underwater on the mortgage), so I ended up renting it out.I only recently got above water on that house, and it is not the best investment property, but I'm keeping it for now since it is finally generating a positive cash flow.I've recently come into a lot more money (self-employed), and am now in a position to buy even more properties, but I want to do it right this time.

I buy in markets that instantly cash flow but tends to be very transient and one of the areas when down by almost 50% in the crash and still isn't back up.

It was right after the crash and we didn't gut it but renovated every room in the house.

I can show you around half a dozen localities in a 100 mile radius of where I live where real estate prices rose during the "crash" of 2007-2009.

@Mindy Jensen Experiencing the same thing on ios, also, after i reply to a message in inbox, it crashes, but my message will go through. most of the time it also happens when i post a reply on a thread, a few times it doesn't crash, but most of the time it does.

NYC has done pretty well for itself and the Bay certainly has a possibility to end up like that, but one could also argue that the Bay and even SF in general has a lot more to do to make transportation as efficient as over there.I'm kind of rambling and going off topic, but basically I guess what I'm trying to say is: a seller's market does not guarantee that the price will go down any time soon, nor does it guarantee that price wouldn't crash any time soon.  

You ask about how to help prevent a loss in a crash.

My only experience in RE if you want call it that , is loan officer/marketer for a mortgage company before crash, I did most of the leg work for the company.

Do you want cash flow or appreciation. post crash there are a lot (more than there were) opportunities for positive flow, with low interest rates too boot.