To be quite frank with you I am sick of discussing it. I feel like a record stuck on the same groove. Day in & day out I answer the question over & over again.
True, I work with mostly investors so this information is in fact, important to them to know. Not crucial though. Let me explain. Investors buy real estate (or stocks or bonds, etc) all of the time, in good & bad markets. They just make sure they are getting the best 'deal' at the present time.
In real estate that means that it matches your criteria. What is YOUR criteria for buying? Are you looking for a second home? Cash flow? A long term investment? Short term? Retirement home? Can you afford to hold the property or are you expecting to have it sold or rented right away?
If you do not have your criteria determined, you better figure it out before you start buying. You need a business plan. Real Estate investing is a business, you wouldn't start a new company without a plan would you? I sure hope not.
To simply call an agent & ask if now is a good time to buy is absurd. We need more information.
Without knowing your investment goals I can't help you. Sure the past couple of years ('04-'05 in particular) it didn't matter what you bought, when or where because it was all going up at astronomical rates. But in my mind thats not investing. That's speculating & most money made during that time in real estate was more by accident.
Now, if you are typical home owner looking to sell, when should you sell? When you need to. It's that simple. People will sell houses in any market, any season, it doesn't matter. The current market, buyer or seller makes no difference. For instance last year those in more entry level homes sold & had gains of $50-100K in equity in only a year or two, they were thrilled. But what could they buy? Everythng else went up to? Many had to leave the area. They couldn't afford the payment to even buy their OWN house back.
This year, I've sold homes for clients who were disappointed about not clearing enough profit. But you know what? They bought another place for way less than they would have had to pay last year. So it all levels out in the end.
If you are looking to buy your first home, when should you do it? Answer: As soon as you can afford it. Don't worry about whether the market is good or bad. What is that anyway? You need a house, the earlier you get in the more equity you'll generate in the long run. Even if you purchased at the height of last years spike, you didin't lose anything. Unless you sold this year. Overall, if you hold the house you'll have equity when you go to sell.