Toronto is a city built from the inside outwards--and this explains its persistent humanism, its resilience, its gritty, half-finished but always living quality and something of its unexpected elegance--the elegance of a Japanese sleeping mat or handmade quilt--a weaving together as opposed to a conjuring up.
OK, I think I am beginning to see what you are getting at... and it appears to be a vast appreciation for toronto's sort of informal, lived-in, loose-limbed and cobbled-together quality, which is a thing that it actually does possess, so at long last we begin to enter the same page in at least this regard. unlike you, though, i don't ascribe this to any overarching culture-based humility or unique local spin. i think, rather, that it is just the natural aesthetic circumstance of a city caught between provincial origins and a megalopolitan near-future... toronto is underbuilt, and it has been forced to make some very rapid, on-the-fly accomodations to its new, swollen circumstance.
let's compare toronto to a city that, for all its differences, has a few areas that are reminiscent of toronto in an architectural sense -- pittsburgh, pennsylvania.
pittsburgh, for all its present mediocrity, was larger and wealthier than toronto until at least the mid-1960s, so it's also a good benchmark of toronto's postwar boom. anyway, were pittsburgh to have swollen into a metro of 7 million during that period, one might expect a similarly ramshackle, informal quality to develop along its streets. formerly sedate rows of duplexes and peaked houses would suddenly find themselves loomed over by towering condos. the empty lots that once surrounded downtown would be bulging with fat buildings trying to eke out just a bit more square footage from the site. formerly countrified electrical poles would lean under the weight of added wires, and would be festooned with millions of posters for all of the bands, restaurants and galleries brought to the city by the influx of new residents.
the overall effect would be... well, it would be toronto. one would be presented with the specatacle of a wealthy metropolitan center that for some reason lacked the pomp and decadence of, say new york. it would be humble, slightly shabby but bursting with oddly-placed jewels. if it was lucky, as toronto was, it would have come of age at the peak of a great architectural movement, and would have a few monuments therefrom (such as CCW and TD).
i think the above is a better fit than politico-cultural theories of torontonian humility vs. american pomp and grandeur. it's for this reason that i regard toronto's present form as a pleasant accident and not an architectural triumph.