As a 37 year real estate investor, for many years I've listened to people bemoan not having invested 20 years ago "when real estate prices were so low" compared with what real estate prices are today.
I recall people in the 1970's bemoan not having invested in the 1950's "when prices were cheap" and I remember people in the 1990's bemoan not having invested in the 1970's "when prices were cheap." Today this pattern is in the process of repeating itself.
What they really meant is that now that they have a 20 year risk free window to look back upon, with certainty they know that was the time to invest. But in the present day, whether it was the present day at a point in the 1950's or the 1970's the unknown scared them away and they took no action.
The present time is the only time any of us can ever act. The past is history and the future has not arrived. So the best time, the only time to act is now.
In the years leading up to the recent real estate crash, Anne and I stopped buying because the prices were so high we couldn't make sense of it and we anticipated they would fall. After they fell, acting with our son Kyle, a very successful real estate syndicator, we came back into the real estate market.
If you can assess calmly and objectively the real estate market or other markets of interest to you, over time you are likely to fare well by choosing the appropriate now, which ironically may well be now as long as you invest for the long term.
What sounds high priced today may look very cheap in 20 years.