“The best time to buy was 20 years ago, the 2nd best time is now”

[Colin Kelley]

I heard the quote, “the best time to buy was 20 years ago and the second best time to buy is now”. I am wondering if everyone still finds this to be relevant? Wouldn’t the best time to buy be when housing prices drop?

[Salvatore Lentini]

Sounds good in theory but if you only bought when prices dropped you'd have a VERY hard time building a portfolio.  You wouldn't have purchased anything in the past 10 years.  And nothing in the 20 years prior to that.  Every purchase I make is specific to the property I am buying.  It depends on the price, the terms, the upside, the taxes, knowledge of up and coming development nearby, rates, rents, how desirable of an area it is, how it fits into the rest of my portfolio, how much time it will consume etc.