Toronto as #1
To add to the personal anecdotes:
I'm originally from Calgary, came to Ontario in the mid-80s for school, spent '89-'91 in Washington, DC, then came back to Toronto to stay, so I've been here for the better part of twenty years.
As part of my job(s) over the years, I've spent a lot of time travelling to Montreal, Calgary, and Vancouver, and some time travelling to Quebec City, Moncton, Edmonton, Ottawa, Saskatoon, Regina, and Victoria. Curiously, no Halifax or Winnipeg.
Both the '90s and the '00s started with Canadian downturns (you can throw in '97-'98 for some in the financial services industry like me, but I don't think that was much more than our industry re-tooling some) followed by booms. IMHO, Toronto won hands down in both cases, growing mightily and gaining ground in almost all commercial and cultural areas versus the ROC. Montreal in the early and mid-'90s was BRUTAL. It took forever to recover -- the many, many boarded up windows on rue Ste-Catherine and general disrepair took more than a decade to cure. (Happily, Montreal is doing great these days, particularly downtown, Old Montreal, and the rest of the inner city -- fabulous to see how much it has rebounded.) Calgary has boomed, but it's such a new city, and so focused on business (oil and gas, naturally) and the outdoors that it's more a collection of suburbs than a city (my parents and brother would disagree.) I agree with the posters who talk about Vancouver as 'small' -- somehow, it doesn't feel like a big city. I suspect the Olympics and their aftermath might change that -- it did (on a smaller scale) for Calgary.
IMHO, there's really only five more-than-regional cities in Canada: Toronto, Montreal, Ottawa, Calgary, and Vancouver. If I was to rank them, I'd go with Montreal last -- Toronto, Vancouver, Calgary, Ottawa, Montreal (people who place more importance on politics would move Ottawa up that list). Toronto is so far ahead of all those cities that it's not even arguable (which is why those who wish to rank things have started comparing Toronto to world cities, so they can feel angst about us losing.)
I live in Riverdale, commute by 504, have a daughter at Moss Park for figure skating and another at Leaside for hockey. My wife is from France, and we can eat as well as in Paris and spend as much of our life as we wish in French. From the languages I hear on my TTC limo, there's many, from many parts of the world, that do the same. That's one of the great things about Toronto.
The other things I think are great about Toronto is the higher culture and the recapturing of our waterfront -- the ROM/AGO/Four Seasons/etc rebuild, as well as the Mirvish/Soulpepper flourishing, and the QQ/WDL/East Bay recapturing of the most beautiful part of our city.
It's been a great twenty years for me, and I think for Toronto. Love this place.