Hi @Rem, very interesting points.
I would say the following (without knowing specifics of other cities):
1. Toronto is surrounded by a Greenbelt, the Oakridges Moraine, and lots of planning policies set in place to slow sprawl, and as such, land is limited forcing Toronto to grow upwards;
2. Toronto's public transportation kind of stinks. As such, we must grow high around areas that have good transit options.
3. What is the downfall of growing tall if there is a strong streetscape and good retail, commercial and employment options nearby?

Hi Matthew,
In response your points,
1. While Toronto does have its own geophysical and geopolitical boundaries, these are things that are not inherent to just Toronto and are representative to most cities in the world (unless we're talking about a place like Los Angeles which is a beast upon its own). I am looking at Toronto from its the point of view of its physical area to population which compared to other cities is quite unique. Toronto is not a large city in population compared to most global cities, but it's a city of incredible physical size. Density is often misconstrued with verticality and is most apparent when compared to some of densest places in the world, which are largely low rise. What I have found interesting is that Toronto (and much of the surrounding Metro area), a city of vast lowrise areas is choosing to create policies of density through towers and not through low rise developments. It appears to be easier to throw up a point tower beside a low rise community than it is to appropriate more land and create a low rise slab development in the same community.
2. To say Toronto's transit stinks is an understatement, its abysmal. After using systems extensively all over the world I can say Toronto's Achilles heal is its undervalued and under funded transit system.
3. There is a lot of pro's and con's of vertical living. Yes if the streetscapes are good and amenities are plentiful there is little to complain about, but there is more often than not a large disconnect of tower to streetscape. As towers get narrower due their crowded lots there is less and less opportunities to develop these base amenities. Unlike Hong Kong, most people in the West are not accustomed to vertical amenity services. This is not to say its impossible, but the European slab development is more conducive to the North American movement habits.
Toronto has always posed a unique character when it comes to its urbansim.

^^In your opinion, does Toronto work? Maybe instead of looking to high-density lowrise successes, urban planners should be looking to Toronto's design?

I agree with ^^ Toronto is growing crowded with towers that look alike and lack in design and quality.

I wouldn't go as far as to say Toronto does or doesn't work. Until the high rise boom has settled and people are living long term in these residences we can then state the success or failure of such construction. One fear is a St. Jamestown reaccurance could be possible. We cannot forget how St. Jamestown was pitched, it was sold to young professionals as a new high standard of living, and they were moved into quite rapidly... 50 years later you be hard pressed to find any young professional who would want to live in them. While our design of condos appear slick and new, St. Jamestown was equally slick and new for the 1960's.
Now I hardly imagine all Toronto's falling into a St. Jamestown'esque condition, but we cannot forget what has happened in the past. While the majority of condo's are sold to single and childless couples, we are going to have to make acceptances for the children of Toronto's future. With the cost of a single bedroom condo on the rise, double or triple room units will rapidly be out of the cost range of most families.
In the end what I am trying to say is we have to wait one complete generation of people before we can say if planners should look at Toronto. If our designs in Toronto can support all spectrums of people; single, family and elderly, then we can honestly and truthly state what is done in Toronto is a valid model of planing.

^^I have a concern, similar to what was said above, that due to the nature of the way condos are sold in Canada, too many smaller suites are being built while in the future there will be demand for larger 2+ bedroom units for families. If this is true, as you said, in the future there will be an over demand for larger suites with not enough supply, putting the units out of reach of families.

^^It would be interesting to see a demographic breakdown of Toronto's condo inhabitants, separate from their purchasers.

The question is not to talk about building height. That question is irrelevant. It's whay are in those buildings and who lives there that is key. For the past 5 yrs buildiders have been designing smaller and smaller units in order to keep the end price within the means of most of. Their purchaserspurchasers are mostly young singles or couples. The average unit size in most downtwon condos (new ones) is under 700 sq feet. We are not building communities that are sustainable demographically. That will lead to serious issues. These buildings could eventually become ghettos when there are not enough single ppl to fill them. Rents will decrease and lo lifes will occupy them.

Matthew said:
^^I have a concern, similar to what was said above, that due to the nature of the way condos are sold in Canada, too many smaller suites are being built while in the future there will be demand for larger 2+ bedroom units for families. If this is true, as you said, in the future there will be an over demand for larger suites with not enough supply, putting the units out of reach of families.

Sounds like the longer term investment play is to buy up the larger units in established well managed buildings.

Hey @Evan, that is what I have always thought. But, as you mentioned, it is a longer term investment so only time will tell if I am right or not!

And this brings me to the bipolar reality that is the present day home, its an 'investment'. No more are the days of where the home was a multigenerational homestead where 'investment' meant the time spend with family development versus the current condition of 'how much wealth' the house brings as investment.
We have gone from the average house costing $100,000 in 1950 (inflation factored in) to about $350,000 (for the mean average of Canada). For most of us, a $350,000 home would be a dream price with the reality of housing costs far above that. The house (condo, duplex or whatever typology) has now become a product in the most extreme sense.
While holding multiroom units will certain bring higher investment values down the road, the real issue is where are the people of Toronto going to live? 40% of the people of Toronto are now classed as wealthy, another 40% are classified as low income, with a measly 20% middle class... that group could be all gone by 2020 at the current rate Toronto is loosing the middle class. With a 50% slit in poor to wealthy Toronto runs a great fear of district collapse. With an incredibly bad transit infrastructure the poor of Toronto will have to inhabit somewhere within the confines of the city ( I should note poor is not homeless, if you make $40K or less, you are now Canada's low-income group, never before has such a level or income meant so little in wealth). These are the people that keep a city running, without them Toronto may have to resort to a New York Rent Control structure to bring back the needed people. However, Toronto's rental structure erodes as the open sales market continues on homes. Rentals have always been the mainstay of great cities. Rentals meant people could come and go from a city with ease, or meant any walk of life could keep a place to live while putting they're limited paycheques towards family and retirement.
I feel I've rambled enough here, and not overly sure where I have accomplished with this entry. After living in Toronto for 7 years I've grown tired of how the city's housing is structured. Working in a profession that requires me to be in the core the city I've grown unhappy with the idea that the majority of my wage will be spent on housing....when it should be spent on my enjoyment of living in Toronto.