If it was a middle of no-where or rural area and the the city is expanding, its practically a gamble on when the price would be right since there market will be providing newer and normally better houses.

It is just speculation aka gambling ,hopIng ,and wIshIng that everything goes up In value over time

You get to recognize how they sound after a while when the tenant is obviously lying -- the landlord is always COMPLETELY in the wrong, evil, monstrous, wicked, the tenant is always COMPLETELY unable to defend themselves and in the situation through ABSOLUTELY NO FAULT OF THEIR OWN, and finally (and this is most important) the tenant NEVER OPENLY SUGGESTS any sort of access to the law no matter how obvious that solution is.

hahaThe reality is that if building owners are not anticipating changes in Legislation to affect a certain building class in the future, they are gambling with their particular asset class.I knew a long time ago (21 years and counting) to make sure I invest only in buildings that has a high probability of never being the target of rent regulated.THUS, this logic continues to push up my building's values.This goes with ANY Investment, not just Real Estate.Take Insurance Companies, for example.

It seems like a better play than gambling on the next two years when we have obvious headwinds to further growth. 

All the gambling whales would travel all different casino in the world. 

I say this recognizing that you are self managing and that in effect makes the 50% rule the 40% rule. 

Too many high flyers, with access to too much money, who are gambling that the Fog City merry-go-round will never stop!...

Rule number 1 "Make your money when you buy" ( If you are hoping to make money when you sell,  then you are not investing you are Gambling) 2 ways to make money when you buy  1: Buy the property well below market value so you have instant Equity.  2: Buy a property and ADD value (rehab,update,or add amenities) If you solely rely on appreciation you could find your self holding the bag if the market turns south.  

You fail to recognize that technology has resulted in more productive workers.