The snarky and hard sell answer is right now, it is a great day to buy real estate? I hate that cliche! It also needs some context because when to buy has a lot of different answers in how the question is put into context to let's try to give some answers in different ways.
Your First Home: I had an agent that started with me to handle the investor resells and he was wanting to buy his first home. I told him this was the perfect time to buy an investment house. He looked at me thinking I had lost my mind. Once he got it he bought his first home that will turn into a great rental that he will keep after he buys his second home. He also got a room mate to pay him to live there so it is only costing him $200 a month for his home. I want him to retire wealthy and this was a great start.
I'm thirty and want to retire in my 50's: By the time I was in my 50's I had over $5000 in poisitive cash flow which doubled once i got into my sixties. The young person can take a steady look at the real estate market and not be in a rush to buy. He can over the course of 25 years get a lot of homes and by the time he is 55 have a few paid off. This type of thinking also means they are doing some other types of investments that build a solid amount of liquid and marketable assets. This will be your true millionaire next door and than book set me straight also.
I'm 55 and I want to have security: You don't have to be young to start but this type of investor is on a faster track. It isn't unusual for me to have them buy 5 homes at a time. Of course these are the folks that have some cash so not everyone can do this. The idea is that real estate gives them more income than they can get from dividends and if they are like me and still working 20 years later, although I have five years to go they can still build up considerable wealth.
I want to buy low and sell high: Don't we all. This type of buyer on when to buy is usally your investor with cash looking for a crash in the market. They are the ones that went to the bubble markets in 2009 and bought at 50% off or more. I don't anticipate this happening again because bubbles never repeat themselves, they move on to a new fraud in a different asset class. But markets like Florida for instance experience market cycles and even if it is 20% off then call me a buyer and an aggressive one.
Know your market types: When asking when to buy especially if you are willing to go outside your local area it is important to know the three types of markets. Oklahoma City represents a linear market that does not have high highs or low lows. It is dependable predictable, and long term. Cyclical markets have a history of ups and downs and Florida is the perfect example. The when in markets like Florida are timing markets. I am seeing owners in Florida finally realizing that double digit appreciation isn't happening every year and want to cash out and take the loss. But in these markets it is like being a day trader in stocks, you need to watch closely. Hybrid markets are more like Phoenix. A lot of stupid money goes into investments in that area. This is when the market is already saturated for rentals and has no where to go but down. Catch these markets on the upswing as versus the downswing like in Florida but don't buy the hype and work with someone in Phoenix willing to tell you no.
In conclusion: I have gone through the five questions reporters ask, who, what, where, how, and when. This is just the beginning of understanding real estate investment. However, there are a few caveats I want to share with you. First, don't bet the farm like putting everything on red in Vegas. Have reserves and understand that you can't be a big winner every time so start conservatively. When an agent tells you that you should buy because this cash cow is a no brainer remember that means you are not using your brain. Run away as fast as you can. As I have said before, don't put all your eggs in one basket. Real estate is not the only place to put your money. Buy passive income and make sure it is passive. You have a life, a job, and a family. When investments demand a lot of your time you know that you didn't either buy right or you would led astray by the agent. The best real estate investments are the ones you forget you have until you see the check going into your bank. That's all for now but like in the picture above, i want you to finish the race a winner.