My official list;
Tall Buildings
Toronto got it's first super tall in 2016, after it being announced in 2012. It is BAC 2, and stands in at 324m. the lead tenant is CIBC, which decided to consolidate its office's scattered across the city. FCP is the 6th tallest building in the city. toronto's tallest building is 386m. It's a Condo built in yorkville at the tail end of the cities extended condo boom, that never really ends, but rather just slowly putters down to a more regular pace of about 15,000 units yearly.
Sports
The pan-american games are (somewhat surprisingly) pulled off without a hitch, leading to a strong olympic 2024 bid. Toronto goes on to win the bid for the 2024 olympics. A new permanent stadium for 75,000 people is built in the portlands for it, and despite the NFL saying it will not put a team there after the games, toronto still gets a team in 2026. The leafs Finally win The stanley cup in 2027, but not after a massive riot akin to the vancouver riots of 2010 in 2023, which is a huge embarrassment for the city, especially 1 year before holding the olympics.
municipal borders
Some of the surrounding municipalities around the city are amalgamated, which include missisauga, vaughn, richmond hill, and markham. Pickering-whitby-ajax become one singular municipality.
Transit
Toronto finally completes the Eglington line, as a partial above ground partial below ground LRT in 2022. The DRL is constructed for the Olympic games, but is not finished until the summer after, leading to the Olympics being a disaster transit wise. In 2030 the pickering airport officially begins construction, despite heavy resistance from the locals. in some weird series of events, a couple of historic farm houses are left in the middle of the airport (in between runways) for "historic preservation". the airport will open (apparently) in 2034. The finch line is finished in 2024. Sheppard is extended as a subway, after much (much, much, much) political strife, in 2026. A high speed rail link that cruises at 265km/h is completed in 2029, running in a route of toronto-kingston-ottawa-montreal.
Politics
Mayor rob ford runs for office in 2014, but gets less than 5% of the vote, the lowest ever for a city mayor running for re-election in canada. All mayors are left wing for the next 4 terms, as too many are scared of letting in another disastrous mayor such as ford. Missisauga Mayor McCallion is re-elected in 2014, only to pass away in office in 2015. a prompt re-election is called, and a new visionary mayor is elected that turns the city away from its old suburban ways, and finally turns it into a fully fledged city. (only to have it annexed by Toronto in 2027)
The provincial government somehow manages to get away with suing the smoking industry for 50 billion dollars, (due to stress caused on healthcare) which it then uses to pay of its now 21 billion dollar debt, fund the Sheppard subway, the HSR link, and to make significant investments in the education and healthcare systems. london also happens to finally get a highway.