Whether or not the deeper cesspool of drugs, violence, crime, corruption, and whatever else many of us suspect to exist is ever revealed and disgraces the mayor, there can be a fascinating story here for a writer. Something like Midnight in the Garden of Good and Evil, where the author uses a factual incident but spends a lot of time telling tales of the colorful characters surrounding it.
Some aspects of the Ford story that would interest me in Doolittle's prospective book:
The rise of the Ford family, especially how the father born into a large impoverished family in East York gained enough affluence and connections to provide a foundation for Ford's rise to mayor.
Drugs - the serious addiction of the sister, the 70's entrepreneurship of Doug and his buddy Dave, the present Etobicoke drug culture of Rob's middle-aged loser buddies and the Somalis.
The competing cultures of Old Toronto downtown and the former suburbs, in how they regard government, how they think about cars, transit and urban development.
High School Football - it's prominence in Ontario versus in American culture, in the time of Ford's highschool years versus now (I think there's a lot less participation and attention, and in many places is being replaced by rugby).
Populism and anti-tax politics. How media has responded to Ford's popularity.