Buying in a Cooling Market

[Aaron Webster]

Hey Canadian investors. Just a general question for those with some more experience in the Ontario markets.

I'm looking to make my first purchase in the GTA or as far as greater PTBO. We're looking to BRRRR our purchase as this strategy becomes viable again as the market begins to cool... albeit only slightly.

My question is general advice regarding this strategy while in a COOLING market. It seems risky to hold a property for a year while housing values begin moving in the negative direction. Maybe this is worry over nothing? Maybe this market simply forces us to take a hit on the reassessment? 

Any thoughts on this appreciated.