I hesitate to jump in to the political debate being so new to this forum (hey, I haven't even taken delivery of my S 100D yet!), but...
Ford will almost certainly win. He can win seats in areas of Toronto that have historically been impossible for the tories to win since the Mike Harris era. Canada, Ontario, Toronto, nowhere is immune to the populist wave, and the opportunists like Ford who are willing to say anything to pander to an oversimplified world view. In turn, prosperity has eluded most normal people, and even though they have access to a relatively high standard of living, they feel ignored, belittled and exploited. People who feel that way aren't inclined to vote for Kathleen Wynne's brand of virtue signalling oneupmanship, even leaving aside the clear history of abuse of power and corruption in the current and immediately preceding government.
These days, whenever anybody tells you that there is no way X or Y politician can win, it's usually because the idea of them winning is so distasteful. The reality is a large segment of the voting population doesn't care about your feelings of distaste. Politicians like Ford are also unconstrained by normal political realities. He is, like his brother, a pathological liar and fantasist whose supporters get a kick out of how much the "elites" hate him. It's not possible to defeat him with logic, reason or policy, and like Trump, at least in an election campaign, he's immune to most of the good arguments as to why he shouldn't be trusted to pump gas, let alone run a Province.
With all of that said, I don't believe even Ford could be worse than the current government. And given that I think Ford is a repulsive individual, that tells you how little I think of Wynne.