That's the thing... architects and developers probably hire people with better taste on average than your median city hall planning functionary.

Now that one is tough too, LOL

I mean look at the median quality of what we've seen here over the last few years.......

I'm happy to (proverbially) throw both sides under the bus.

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There are ways to 'regulate' aesthetics, to a point, effectively. But aside from enabling legislation to do so; its not a small task to set it up, and any process will add a layer of approval (think of it as mandatory design review) which could easily add months to the typical approval.

It doesn't have to............

IF you look at Paris, France, it is very prescriptive in its designs in many areas. If you comply, the process isn't unduly onerous.....errr, for France.

But what makes it 'work' is a very clear description of roof-style, window-style, material, colour etc. etc.

You need something of a public consensus on what should be required........but you will, to some degree, stifle innovation. Whether you add cost or not is an interesting question, as a prescriptive system can result in more people making fewer designs of windows, doors etc. which can lead to more price competition, Its all very complex.
 
You also need to remember that 28 floors isn't particularly tall, for Toronto...
Yes, but location matters. Three 100-meter-tall buildings in the middle of a residential neighborhood where the max height is 12 meters isn’t ideal. Instead of that, we could build a couple of 6-story apartments that wouldn’t disrupt the character of the neighborhood while still housing the same number of people. Look at the West Village in NYC, Montreal, and Boston — they effectively house more people than Toronto in a smaller space without needing tall buildings like that. The smaller building on the west side of the development seems like a much more feasible option for the neighborhood.
 
Yes, but location matters. Three 100-meter-tall buildings in the middle of a residential neighborhood where the max height is 12 meters isn’t ideal. Instead of that, we could build a couple of 6-story apartments that wouldn’t disrupt the character of the neighborhood while still housing the same number of people. Look at the West Village in NYC, Montreal, and Boston — they effectively house more people than Toronto in a smaller space without needing tall buildings like that. The smaller building on the west side of the development seems like a much more feasible option for the neighborhood.
I think your own example explains why your vision for the city is not being built. The West Village in NYC is extremely expensive - a quick Googling shows that most properties are in the tens of millions of dollars. This Mirvish development was meant to provide housing for renters. (And, has been noted, it is even a little expensive for that!)

As well, to build enough 6-story buildings to match the density of these few tall buildings would require the destruction of many more single-family homes. I'm all for the destruction of single-family homes (I think it's bananas that we have streets filled with them literally meters from our CBD), but this is literally an unwinnable war in a democratically elected city. No councillor would last more than one term if they tried to push for the wide-scale destruction of single-family homes required to make our city look like the East Village or Montreal. Many of the people living in these dumb buildings are too fixated on the idea that they can live a suburban life in the downtown of one of the largest cities in North America: backyard, on-street parking, only houses around them.

I would also point out that "disrupt the character of a street" is exactly the sort of argument that is made to keep these homes, so I think you'll need different talking points if you want to get people on your side. (I'd also point out that the idea that buildings can "disrupt the character of a street" is really just NIMBYism in a better outfit.)
 

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