I think a lot of it comes from Ford's appeal as an 'honest man'. People take his word for whatever he says, and that's where examples of your friends come from.
The first step to breaking that claim of honesty. As long as Ford remains 'honest', people will continue to believe. People need to lose faith in Ford, and this should be done by providing examples of how many times Ford has lied and has been dishonest. People need to come to a point where they think, "Is Ford telling the truth, or is he lying?" Obviously Ford lies all the time, but rarely is it directly pointed out.
City council ought to do the same in loudly pointing out that Ford is a liar. Denzil MW took a great first step yesterday in calling Ford a coward. City council's always danced around the issue, preferring to talk about city issues instead when Ford has made the issue about himself a long time ago.
The second element is to break his claim of being fiscally responsible, which is the core of his message. Bonus points if you can combine the two together. Never raise any social issues. The big issues in this city are about money and transit, not social programs or the homeless.