Personally, I remember vividly being in a similar position wanting to buy in 2006, I could not find a deal but luckily didn't force one, so when the crash hit I was already educated with the local market and sitting on a pile of cash that I had been saving to invest.

And of course pre crash was some of my best years so it worked out tax wise quite nicely..

Even in Echo Park which used to be known as a gang area average home price is $800,000 ..As others mentioned many buyers bought when homes were a fraction of the current price .In the late 90s home were 1/3 of the price or less .During the crash homes were about half of what they are now even .

Those markets tend to crash much harder in a downturn, but then appreciate much faster when the market turns to close the price gap a bit more, but the average appreciation (over several cycles) tends to be lower ... so, the best time to buy in these type markets is actually after a crash, but that is not to say that it can't work today so long as you put in the time and effort to find a great deal before pulling the trigger, which to me is the cardinal rule to follow in any market at any time in the RE cycle.

To be overly general, one group almost seeks signs of an upcoming crash and the other tends to operate based on FOMO (fear of missing out) because of real estates performance over the last 7-9 years.  

So I was actually still crashing at home - I put in the offer a month or two after graduating. 

Even if paying many times over the price for the multifamily than the value of your present one unit home.The repercussions of any fraud, or of engaging in ‘non-permissible’ practices, can carry severe consequences, especially in the mortgage world that we live after the 2008 financial crash.

Had you not used leverage, you'd only realize a 20% gain.What most people fail to mention is that this also works in the opposite direction, as we saw during the RE crash.

I get asked that same question all the time about my properties...Truth is with my San Francisco properties, they drop 15% in the last crash, and it is hardly worth the in and out....If, on the other hand, you are in an area that dropped 50% in the last cycle, I would look into selling now, as you could easily buy back at 20% less a few years down the road...

The CV (& IE) started crashing in '06 and have since recovered.