"As some have mentioned Toronto definitely does not have a reality problem--just a marketing problem. "
Good post by allaboutmatt, I certainly agree with a lot of it. I think the above statement is definitely true, and I think a lot of TO's negative press is based on old preconceptions of the city which increasingly no longer apply. It certainly is painful to hear from people abroad that still perceive Toronto as dull and corporate- 'yikes where have you been?'- and Montreal as more vibrant and cosmopolitan. So I agree that a lot of it is marketing and making the world more aware of Toronto.
But I think Toronto's appeal abroad is something that is going to take a lot of time to evolve. Montreal has a more mature image as a city abroad- as does Chicago. Perceptions of places are often based on the arts, culture, and food that are inherently associated with the city or region. This is something that can't be fixed- it has to develope over time.
"Let me explain what I mean, in the North American context, based on now almost 5 years of living in the US. If you take New York out of the equation (and you should, since it is and will remain in its own, very small international league with London) there is not a single city on the continent--not one--with as much going for it as TO."
True to some extent, although I'm sure there are millions in Chicago, San Fran, NYC, Los Angeles and Montreal who would beg to differ
Toronto is a very well rounded city in that it has a little bit of everything that most cities in NA can't boast. But people's perception of cities as travel destinations are not based on their livibility or how well-rounded they are. The fact is that Toronto IS competing today and tomorrow with these cities for tourist dollars, so Toronto does need to concentrate on things that it doesn't do well. Aesthetics imho is definitely one of them, particularly in the form of beatification projects, develope it's natural assets such as the waterfront, improve quality of architecture, adding and improving cultural attractions and parklands, and perhaps by including one or two unique attractions that can't be found in these other cities. Another idea might be to dedicate a pedestrian street somewhere downtown to restaurants etc. These are the things that TO needs to continue to do in order to maintain pace and compete with the likes of Chicago and Montreal. But i agree that TO is definitely on the right track but, again, there are also definitely areas where the city is lacking and not doing as good a job as others.