Anytime IS the time to buy real estate... its not a matter of time, but PRICE.
You cant buy low and sell high if the market is going down without waiting a LONG time for the market to bottom and then turn back up.
I would not want to buy the $400k house today that will be worth $300k next year.
One can make a fairly accurate assessment of current market value, but it might be more difficult to determine tomorrow's market value.
If you are INVESTING in a stock, in order to buy low and sell high you need to pay a LOW price for the stock. One of my sons tried to convince me to buy 100k shares of his favorite tech stock - AMD - when it was $69.00 in 2000. I told him that I would not pay that price for the stock and I put it on my watch list and watched it sink all the way down to $3.00 where I was considering buying it - but didn't. (wish i did.) Where is Real Estate any different? In order to buy low - you either need to wait for the market to bottom or you have to have an investment strategy that protects your downside.
WATCH YOUR DOWNSIDE - THE UPSIDE WILL TAKE CARE OF ITSELF
Property XYZ is on the market for $250k
I think the property would sell for $200k (thats where the retail market is TODAY)
so, if I want to buy low, and I do, I would say in most markets that 65% LTV is a safe offer, so an offer of $135k would be my highest offer. Since the market is spiraling down, today's offer would likely be $100k
so, at $100k I can buy low and sell high. If i go in and pay market price of $200k and it goes down, there is no margin for error.
Having said that - this does NOT apply if I need a house for my family. If I need a house to live in I'm not going to worry about all that - but then again - I'm not viewing my primary residence as an INVESTMENT. If I did then when the value of my house goes up I would sell to take profit, but when you have 6 kids (3 still living at home) you're not likely to yank up stakes just because your house went up a couple of hundred k.