John Tory will win. Sorry to spoil it so early, but all the signs point to a fairly easy victory. My prediction would see something like this:
56.97% - John Tory
32.32% - Jennifer Keesmaat
Why those exact numbers? That's what David Miller and Jane Pitfield got in 2006, when the general feeling was the same between the Left, Right, and Swing voters. "We sort of like the current Mayor and want to keep them, but they really have not build as wide a consensus as we'd prefer, and will vote for an opposition candidate strong enough to ensure the Mayor actually has to campaign"
I've been attacked before for suggesting that Jennifer Keesmaat is like Jane Pitfield because both are female. As I said then and as I say now, their gender has nothing to do with it. Both are simply "fillers" for a 'side' (left or right) that needs a 'candidate' to vote for. Had the left put up a candidate in 2000 against Mel Lastman, I'd have expected a 56.97%-vs-32.32% split, or something similar. The numbers "56.97%-vs-32.32%" are simply a representation of what happens when swing voters are happy enough with the current Mayor, but people on the opposite end of the political spectrum are not.
As for how council turns out, that's another story.
Polls are rare, if not outright non-existent, and, as such any prediction is an outright guess. Regardless, here is my guess:
While not terribly effective, this situation is not ungovernable. Tory has straddled the middle before, and if he can use the Left against the Premier, and the pro-Ford councillors against the Left, he can govern effectively. In fact, doing so would probably lead to a third term for him. Tory's problem is that the Left really does not like him, and he may find them unwilling to help him in battles with the Premier and the Ford-allies on council. Such a scenario would likely result in the "Ford Squad" on council organizing, and if that happens, Toronto will be more dysfunctional than it was with 44 councillors.