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The NYT calculator is one of the dopest data products they've come out with. However, it doesn't paint the whole picture. Macroeconomically speaking, we're in a bubble. The Fed is all out of instruments; rates just can't go any lower and if they go higher all sorts of shit in the stock and bond markets is going to shake out to a loud crashing sound. Not to say prices are going to go higher; not to say prices are going to go lower. Whatever they do, they're likely to do it slowly.
Microeconomically speaking, individual markets are a lot more volatile than they used to be because states' rights and local housing/wage initiatives are really fucking with things. Your town may be headed for a downturn or it may spike. And if you don't know how long you're going to be there, your odds of ending up upside down exceed your odds of ending up right side up.
Don't ask "should I buy A house." Ask "should I buy THIS house" because there are many reasons to maintain the flexibility of a rental and it's foolish, in my opinion, to grab a large piece of real estate you know little about in a location you aren't familiar with. Also keep in mind that unless you're shoveling in a great deal over your minimum payment, the balance on the mortgage after five years will be virtually indistinguishable from the balance on the mortgage the day you got your keys. You are effectively renting... but you're renting from the bank, and you'll face ridiculous fees if you want to break your lease.