Answer that question and you'll have quite a career in political consulting!
IMHO the Fords' popularity is tied to the socioeconomic exclusion experienced by a growing number of people in Toronto as well as many other places around the world. It's a reaction to the perception (not terribly accurate, though not wholly inaccurate) that a small elite, both economic and cultural, has rigged the political system to their own advantage.
This perception doesn't fall neatly into the categories of left/right wing. It's more like an us/them tribal identity. It's why this constituency will vote for Harper, Wynne, and Ford without feeling contradictory. It's why they won't vote for Chow, despite her policies being the most effective at combating the inequality that incites their anger. It's also why they see a millionaire like Ford as one of them. It's not about policy, it's about perception.
*takes academic hat off*