Great work dencity.
Rather than submit alternatives, I suggest we build on this... if you are willing to consider some suggestions.
1. The font choice is perfect as is the uppercase. Interesting that you bolded urban rather than Toronto...
2. Colour
I'm kinda torn about the colour scheme.. on one hand, I wish it had more punch than black/grey (as you may know I have a thing about "lack of colour")... on the other hand, too much colour might make it look too much like cheap clip art, since the drawing style caricatures the skyline... I'm conflicted.
Since the logo will likely be used most often as a gif than faxed... I think it definitely needs a shot of colour. We don't really need a b/w logo though this would lend itself nicely to a b/w version anyway.
3. The Maple Leaf
I'm ambivalent about this but this idea is definitely overused. Everyone knows Toronto is in Canada (so far!) and I am extremely patriotic... but I think it is superfluous.
4 suggestions:
1. Change the font colour so the name jumps. Perhaps you could keep the bold grey "URBAN" and pick a colour for TORONTO.
2. Try other one colour versions for the skyline
3. Try one that hints at the actual colour of each building (not literal)
4. Ignore these suggestions 'cause it's great.
This is getting picky, but the only thing missing from the buidling icons is something historical. It's cliche but some of the Royal York would look very nice front and centre.