Tulip trees can be found only 2 hours away...near Turkey Point. The Carolinian Forest trees (Tulip, Sycamore, Sassafras) are all found in Ontario and quite striking.
It's a shame that the City does not understand the different microclimates throughout Toronto. They have a list of about 20 trees that can be planted in the ravines but assume that the Humber, the Don and the Rouge all should have the same trees (as well as the North and South end of these ravines are quite different as well). There are also clay and sandy soils in the ravines so trees should be picked accordingly.
The city also demands a deposit if you are trying to cut down Norway Maples in your backyard to plant native trees. They should be encouraging this.
Sometimes I really questions the cities judgement on trees. I saw a crew planning some evergreens...they just finished planning cedar's at the top of the hill and were planting pines near a river in the park. I asked them if they got them reversed and they looked all confused. As I expected 2 years later both were dead.
There are many knowledgeable staff in the city's Forestry dept. Though admittedly this is not universally the case.
There are competing views on how do certain things; as well as third-party pressures.
To top it off, the example you cited may well have been poor site choice for the trees but I could easily envision that being successful. While cedar is often found in bog/swamp like habitat, it can actually withstand fairly dry conditions and poor soils; what cedar doesn't like is competition, which is why you often find it where other plants can't or usually don't grow.
Red Pine is often found in sandy soils atop bluffs and cliffs, though it can be found in other conditions too; white pine on other hand likes riparian habitats (river-side) and can often be found in lower land areas. See the extensive stand along the shores of Cootes Paradise in Hamilton, where the bald eagles nested last year.
Bloor was a case of a third party pressure as there was a desire to create an 'allay' of the same tree species, someone saw it done in Europe or the like and wanted to replicate it here.
The errors were two-fold, wrong species for that area. London Plane can do ok in Toronto, though, it may have a harder time than in a more temperate climate; but Bloor St. was just not a good fit. I expect (but don't know) that salt levels were a factor, but also the cold, and the wind tunnel effect on Bloor.
The second error (arguably) is going with any one species for such a long distance. Toronto has had the experience of streets mostly lined by mature elms, which were all but wiped out by Dutch Elm disease; more recently, Emerald Ash Borer has resulted in large swaths of Ash trees, particularly in 50s/60s era Scarborough and North York coming down and leaving a veritable moonscape behind.
However pretty it may look, going w/all one species is high-risk, because one disease or pest can wipe them all out.