I'm sure you already know this, but, the main reason Tory won all of his subsequent elections, and would be favorued in this one, is name recognition. He won because he was a milquetoast alternative, people wanted to avoid drama, and then became the default option. Same reason why Chow is ahead now. Incumbency is a strong advantage in municipal politics, and I would be surprised if whichever candidate wins this elections didn't have smooth sailing in the next few elections as well.
Yes, because, that is a pretty big lapse in judgement. I also have a family member with a DUI, and while he is enjoying his life, he wouldn't be the first to come to mind to run the city.
This part is obviously based on personal political preferences, but, yeah, we need someone to pick a fight, and shake things up in council. Council has been completely devoid of good ideas for decades, on both left and right. We need somebody to knock heads and shake things up. Oh, and if you are sweating Olivia Chow creating problems or picking fights with Ford, I would rest easy. Extremely unlikely. Modern NDP makes some noise on social media and on CPAC, but cowers away when things get even a bit heated.