Reasons why Toronto is bad:
1) Bad public transportation. This is the fault of both the city management and the province, but the TTC went from being the best public transportation system in North America to somewhere down in the 30s. Considering there aren't that many large cities in NA, you do the math.
2) A focus on getting big events. The Olympics in Toronto? Commonwealth games? World Fair? Considering that the waterfront is undeveloped and major infrastructure, including a direct rail link to the airport, does not exist, this is just ludicrous. The idea that a big project would suddenly get these projects built makes no sense, given that the city is close to, if not already, in debt anyway. It took Montreal 30 years to recover from Olympic debt and their biggest legacy is a stadium that is falling apart.
3) Fighting the Island Airport. Given the lack of a direct link to Pearson, the fact that the Mayor has gone out of his way to attack the island airport is just insane. Although, it had the good side effect of killing the World Fair bid, since Miller was too busy fighting for a photo-op rather than attend to the business of city improvement.
4) Pitching Toronto as a world class city. Spending money to convince New Yorkers and other Americans that Toronto is some kind of world destination city. Diversity is pitched, but when it comes to actual events, it's always the same Mirvish crap and Leafs games. It's doubtless that Toronto has a great music and theatre scene, but if you live in NYC, why would you bother?
5) Killing downtown. Somehow building condos downtown will revitalize the core. I don't understand this logic, given the fact that there's a huge fucking strip club just south of Bloor on Yonge (the one where every male celebrity comes out of when they bother to come up to Toronto), putting condos downtown won't suddenly make it a place to go. Dundas Square is a good idea for a civic space that's easily accessible, but it's ruined by the fact that it's become billboard central.
6) Urban sprawl. This is a problem in all cities, but it's also a problem in Toronto as well. Because public transportation can't keep up (where's our BART? Go Transit? Really?), traffic clogs up during rush hour because no one wants to or can't afford to live in Toronto itself.
That's just a few reasons why I think Toronto is broken. Don't get me wrong, I'd love to live in Toronto simply because there's just more to do there than anywhere else in Southern Ontario (other than Ottawa), but it's a hate-love thing. If there was one single thing I could fix with a few billion dollars, it would be the public transportation. There was an hypothetical subway map that showed a TTC with 10 different lines. Now, that's unrealistic, but improving and expanding the streetcar lines would do so much to improve the city it's ridiculous.