Yep, looking at the bylaw, the growing medium - soil - is only required to be four inches deep. Weight of soil and drainage starts to be a problem - you have to figure that the soil may be 100% soaked...
It's going to be tough to grow trees in four inches of soil.
So, nutshell, tree survivability not a problem, but engineering a roof to hold enough soil (and therefore water) to grow a large tree is expensive, and root damage is a problem, and therefore - no large trees on skyscrapers. Still, there's nothing magic about it, just engineering problems. I could easily imagine a high-end residential tower with a forest on the roof.