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Winnipeg's a good example of preservation through stagnation. Toronto's probably one of the best examples of being a victim of your own success.

I wouldn't say that. Witness Eaton's, or some of the historic factories and warehouses along the Red River and the railways to the north of downtown. Portage Avenue is pretty ugly along much of its downtown length, but to the north, the Exchange District is charming, and apart from the Forks/VIA/Fort Garry area, a lot of the built heritage is gone, perhaps in the Detroit-type mindset of "demolition means progress" (the actual slogan of MCM Demolition, which is very active in Detroit and Flint).
 
Antiloop33rpm, it seems that you're making Kingston out to be some sort of depressed, stagnating, bible-thumping backwater, while i've always thought of Kingston as more of a slow growing, socially progressive, sophisticated and well-rounded little city with one of the most well preserved and vibrant downtowns in Canada.

Are you being too hard on Kingston, or am i way off base?
 
^probably somewhere in between. every city has sprawl, and kingston definitely has one of the most vibrant downtowns in ontario - my pictures were taken on a cold sunday afternoon in february and there's still lots of activity. and i haven't seen a downtown gap in any city that small. but it has economic problems - the city's having a hard time paying for infrastructure and the population is only growing because of the far flung suburbs. the actual city (pre-amalgamation) is shrinking.
 
I think Montreal's just lucky that someone decided to build the new downtown several blocks north of the old city.

For lack of a better reason, that is exactly what happened. There is no doubt in my mind that Montreal would have had the same orgy of destruction with respect to historical buildings as Toronto did. The north western portion of Old Montreal has a few signs of this. Add to that, the Ville Marie could easily have cut through old Montreal along the port. Even its present location was widely criticized during its construction.

Montreal lost more than few architectural gems during the 60's boom period.
 
There's a great old book called "Lost Montreal," which shows some of the streets and buildings that were demo'ed in the 1960s. Many of them are really, really gorgeous. My dad (an MTL expat in T-O) keeps it to look at wistfully from time to time.
 

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