Why did we elect him?
It's worth mentioning that the voter of the old city of Toronto did not elect him. It was the voter in the part of the city that joined with amalgamation- i.e. the more suburban, car-driving people. Ford is from Etobicoke which was its own city not too long ago.
People voted for him because they like his message of being fiscally responsible. It was clear that he was ignorant, compassionless, and not suited to be mayor of the biggest and most diverse city in the country. He promised to cut taxes AND balance the budget without any service cuts, which was clearly never possible and by now it's hurting us. He had a simple message that resonated with people and most people don't read the newspaper and didn't bother to pay enough attention to really have known anything real about him.
Many voters base their decision on little snippets they hear and how they happen to feel about the candidate. I think that that is largely why he was elected.