I think that the time for something like this is now: Google/Alphabet has the cash and Trudeau, although I don't necessarily share all the irrational exuberance about him, seems to be the kind of thinker who can push this sort of idea at the federal level. As Scooter said in another context, hating Toronto is a Canadian national sport and that bit of the Gardiner Expressway is pretty ugly - think Boston before the Big Dig - but this could be the start of revitalizing North American cities to make them liveable in the rest of the 21st century.
But there's a danger in making a city too friendly and if Google can resist the urge to try to monetize everything it will be better for all concerned. Google and some of their people may have the wit to see this. There is a paragraph on the subject of privacy:
Part of the joy of city life is that you do not have your favorite song playing in the elevator: you have someone else's choice. You might hate it or you might love it but it's the essence of serendipity that you run into stuff you do not expect. I like the convenience of Wikipedia; but I have to say that I miss the experience of an old book encyclopedia where you can be looking for information on Hank Aaron but be sidetracked by the lovable aardvark.Not everyone is convinced. To make a service smarter, or more user-friendly, you generally need more information. Let's say someone clambers into an elevator; with a motion sensor you can detect their presence and light up a control panel. If you know who they are, however, you can also play their favorite song or take them to their hotel room automatically.