Buying at the height of market isn’t so bad

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I keep hearing how it is a terrible idea to buy at the height of the market. My premise is that if you are doing a buy/hold longterm then it shouldn't really matter if you are buying at the height. In some parts on California you could have gotten a house for $120k at the height of the market, then they went down significantly but but time the 90's and 00's rolled around these same properties are now worth over $1M. That is not a bad deal at all.

Convince me otherwise.

I'm not going to try to convince you otherwise, but I will point out that when the market trends down, there are risks:

-  Rents can drop
-  Vacancies can increase
-  Banks can call loans due
-  It can be difficult to refinance

So, make sure you have reserves to cover a short-fall and ensure that your loans are long-enough term that you won't have to refi short-term.