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I'd rather be homeless than live in a condo...but I do like watching attractive ones get built...like Woodwards, 42 in Waterloo, and anything by Daoust/Saucier+Perotte/Nomade/aA/Teeple
Toronto definitely needs something in the 400m-450m range. Or maybe a little higher on a par with, for example from the picture posted above, the Shanghai WTC. Then with the addition of a few more towers in the 300-350m range, the skyline will begin to look even more impressive on the world stage.