I definitely have to agree with VTB, but I have to add an important point. While Ford was born with a silver-spoon and has never felt poverty, he also possesses the ability to connect to the everyman in a way other politicians in Toronto have not been able to. It's the Ford Fests, the 311-esque phone calls, the radio shows, the personality that creates this sense that he's one of you- it's the same feeling you get when you learn that someone important has something deeply in common with you, i.e. a celebrity having the same hobby as you do. It's empowering to feeling that someone high up will deal with you problems, not a lowly clerk.
Does this really translate to any positive policy making? Not really- I haven't really seen any overhauls in city management (outside that foolish across-the-board cut), nor have I seen any official strides made in terms of efficiency or customer services. To Ford, the big city issues like transportation and poverty are all social engineering- he believes the city can be fixed one citizen/subway line at a time, or better yet, the problem will sort itself out, free-market style.
But to people who support Ford, this doesn't matter because their problems were solved; the rest of the workers who run the city, the clerks, bureaucrats, the planners, the garbage men, the utility workers; they are all grouped together as part of "the problem". None of their work means anything because to his supporters, Ford will be the hero who saves the day.
I'd believe that somone like Tory has a better grasp of the bigger issues facing Toronto from his term as head of Civic Action, but connecting to the people will be something that he'll will need to overcome. I'd hope he begins hosting a few festivals of his own.
Ford has been the primary one propagating and profiting from stoking the divisions in the city, it only suits him that some of the vitrol he spews out splashes back.