[Drybrain]

Toronto: I remember five years ago, visitors from Montreal talking about how Toronto was coming to equal Montreal’s vitality. I think at this point it’s surpassed it, absolutely—the idea that Toronto has reached some kind of urban singularity or threshold feels true. The city feels massive and alive in a way that it didn’t even very recently. The arterial commercial streets are packed with people in a way they never have been, and there’s a sense of a deeply lived in place, everywhere. The built typology of the city is inferior to Montreal (duplexes and single-family houses next to massive towers) but it’s transcended the limitations of its built form by sheer size. It’s a complicated, highly imperfect, but great city.

I don’t think the criticism that Bathurst Street is sleepy are very fair; Bathurst is mostly just front by houses. Dufferin is the same. But visit almost any other arterial, either north-south or east-west, between the Don and the Humber, and they’re very lively, and much moreso now than the recent past.
Criticisms: More than ever, Toronto has zillions of cyclists, but the infrastructure available to them is still pretty crappy.

The cost of living, as well, is already contributing to serious income and ethnic segregation in the city, and right now the city is not doing enough to address it. Ultimately, that could put the brakes on its vitality.

Montreal: I can’t really speak to Montreal intimately, except to say that I’ve never felt like the city was culturally closed in a way that I don’t feel, at this stage of life, I could overcome if I moved there. Most of the people I know you dearly love Montreal grew up there, or went to school there, at that time of your life when you’re forging those tight, tight bonds. It is an incredibly distinctive place with a great character all its own, but as a visitor I don’t feel especially welcomed in to become part of that.
It is an incredibly well-built city, of course, easily the best urban fabric in Canada.

Halifax: I disagree here, I think it does feel larger than it is, especially in the past few years. Probably not compared to European cities, but definitely compared to comparable North American (and especially Canadian) cities. It’s been undergoing a smaller-scale version of Toronto’s graduation to a new plateau.

This summer has been great in Halifax—neighbourhoods that in years past were mostly sleepy are packed in the evenings, downtown and Spring Garden Road are thronged, many (certainly not all) of the new developments being built are huge improvements to the urban environment and creating both more residential density and more of textured and interesting visual environment. Many of the farther-flung bits of the peninsula feel more connected to the gravity of the city centre, and are building up small nodes of mixed-use development, both new and renovations of older buildings, that are creating the feel of a more contiguous urban environment across the peninsula.

Totally concur about the heritage losses. The specific ones you mentioned (the pitiful state of Young Avenue, and the Spring Garden Road block torn down for a fairly generic new development) are absolute unnecessary and lamentable.

Overall the city is doing really well, though, and on balance it’s a good city that’s getting clearly better, and more urban.