Like many people on HN, this has hit us hard. I had just finished grad school in 2008 and was single - it was unclear if buying a house/condo made sense then. Fast forward 5 years ... married, jobs, ready to settle ... except now, everything seems pretty expensive. Okay .. lets wait it out. 2013-2016 ... prices keep increasing. Everyone and their uncle is investing in real-estate. REIT are scooping up properties and collatorizing the rent payment. If we had taken a mortgage, our monthly payment would have been fixed but with rents, it keeps going up. I also did the math ... I paid about 180K in rent (averaging between 2500 and 3K a month in places where I lived). I have nothing to show for that.
Of course, we all make our own decisions. We have decided to buy (at what may well be the top of the market). We had a need to buy in 2013 and I wish we had not let "expensive prices" deter us. The monthly payment argument was as valid then as it is today. If/when the market turns, we'll buy a bigger place. Right now, we're buying a small starter place and at take a stab at the American dream. That's the logic I'm using. I really wish real estate wasn't causing so much misery but it is... I can't outsmart the market :(