Keep in mind that these cycles tend to be longer than most people think. 18 years is the average for the US, so if you're going to sell at what you perceive as peak, you should consider if renting an apartment fits your family lifestyle for an extended period of time. Might not be a big deal if you're a single person, but it might be if you have a family. So that's another factor to consider. Sometimes we need to factor in emotional aspects of life when buying.
You also might want to do some math on how saturated your market is too. i.e. in Toronto, the fact that they've started building 4 units per person projected to move to the area every year for the past five years is just one thing to consider. This didn't seem like a problem to market participants that sent the market up another 56%, which some people are probably kicking themselves over. The fact that high-ratio mortgages started to look saturated at the end of last year however, may be an indicator that this will change in the near term. So just because you're seeing overbuilding, doesn't necessarily mean there's going to be a top soon. You should search for something that will trigger the change in mindset for the local market.
Also worth considering, if you liquidate your primary residence and are waiting for cheap property to start appearing, what's your inflation hedge to ensure that the money you just made doesn't decay in value?
P.S. I wrote the article you're referencing, so there's a definite bias towards cycle perspective. Not necessarily advice, but things to look for when considering your market. Long time lurker, first time poster.