The buyers who do well are almost always the ones who watched a specific pocket for a month or two before they were ready to write. Not browsing: watching, with a record.
What to track
Listed price and sold price for every property that matches your criteria, whether or not you liked it.
Days between listing and sale. When this number starts climbing across a whole pocket, your leverage is improving.
Whether there was an offer date, and whether the property sold on it or afterwards. Failed offer nights are quietly informative.
Terminated and relisted properties. A place that comes back at a lower number three weeks later had no takers at the first one.
Seasonality in the GTA
Broadly: February through May is the busiest and most competitive stretch. Late June through August thins out as people go away. September and October pick up again. Mid-November to early January is the quietest period of the year and often the best time to be a buyer with patience.
Go to open houses in your target pocket even when you're not ready. You learn what $900,000 actually looks like on that street far faster in person than in photographs, and the photographs are professionally lit.