Dundas Square is essentially an empty space--that's a good thing and a bad thing. Let's start with the good: I'm a big fan of open spaces in otherwise crowded, downtown environments, and the urban-planning mess of lower Yonge was crying out for a bigger vision. A whole bunch of squalid buildings were torn down, and bigger ones built ringing the square.
Now for the bad: the new buildings consist of the typical corporate mexaplex crap, and won't age very well. And Dundas Square itself is little more than a concrete plain; there's little in it that distinguishes it aside from a few fountains and a curvy portico that looks like an OCAD class project.
I actually think comparisons with Times Square are rather apt. In both cases, notorious sleaze has been swept away in favour of soulless retail commerce, and a little local colour was lost in the transition. Look at Trafalgar Square in London to see how to modernize an urban square for the twenty-first century.