IMO, topics like should Yonge and Dundas square keep improving on what it already is, and how it relates to urbanism is yes. They've already committed to making this area this flashy centre point like a Times Square, so might as well keep going down the path of doing it right. Call if a knock off of New York or anywhere that something this, but if were going to have one of these areas, I'd rather the rest of the world think it's pretty cool then some lame half ass attempt to have one of these kind of spots.
YDS is not a heritage space. It was not always this way.
In point of fact, it didn't exist until 2002. I happen to think it looked better before (which is not to say good; but certainly more urban and edgy)..
Regardless, just as we (Toronto) took down a lot of buildings to make way for the Square and what surrounds it (10 Dundas East)..........we can (and should) start over again.
We made a hash of it. It didn't work out. No shame in admitting that and moving on.
The billboards never made it amazing and never will; they add light pollution and crass commercialism without giving anything back.
The Square itself is also banal and has a poor relationship to Dundas Street East.
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As apart from that, and as stated before, I happen to like much about NYC, Times Square is not one of its better features in my mind.
But even if it were, I wouldn't want to duplicate it here. Should NYC build its own CN Tower?
Let NYC have Yankee Stadium and the ESB and the Brooklyn Bridge and Times Square.
Let Toronto be Toronto, just a better version of itself.
My take on how to improve the Square itself is one I've already given in this thread, so I won't repeat it.
As to 10 Dundas East, level it, and the Ryerson parkade.
Rebuild the O'Keefe Brewery (to its original design, but allow for adaptive re-use), rebuild the Biltmore theatre, rebuild the hotel at Yonge/Gould Let Toronto's recreated historicity sing and contrast
with the Eaton Centre, which should likewise see the original Dundas entrance restored, instead of the cluttery crap that's there now.
In the alternative, design something new, but let it be the subject of an open, invited, architectural competition, with critics taking first cut, and a top 5 choice going to a public vote, no value-engineering allowed.