I know very little about Toronto politics, but I'll give my 2¢ as an ill-informed outsider anyway. I feel it's not unreasonable to weigh in this way, as probably most voters are even more ill-informed than me, unfortunately.
I'm thinking Josh Matlow is unlikely to gain much traction going forward. This on the surface at least seems to me like a Chow vs. Bailao race, with Chow getting Toronto Downtown support while opposing the move of the Ontario Science Centre, and Bailao getting more even support across the city while supporting the move of the Ontario Science Centre.
I must admit I was initially a little surprised Bailao got the support of some unions over Chow, but then again it might have to do practicality and optics. Bailao is centrist (or perhaps slightly left) but maybe has a perceived advantage to negotiate with both the right and left, something that may play well in places like Scarborough and Etobicoke. OTOH, Chow is just firmly left, and with a strong Downtown bent. Chow got the endorsement of Gil Penalosa, but I'd say that the vast, vast majority of Torontonians don't know who he is, and don't care either. And having the support of Kristyn Wong-Tam won't help getting those inner burb voters who are centre or centre-right leaning.
BTW, I have no idea if this post is flame-worthy or not, but it's just how the situation looked to me as of today.
P.S. Off topic but I liked
Queenmaker on Netflix. It gets ridiculous at times, but I found it quite entertaining nonetheless. It's a Korean TV series about a fictional Seoul mayoral by-election, featuring a very left woman as the underdog protagonist.