Toronto 75 on The Esplanade | 99.97m | 29s | Harhay | a—A

Colonnades only really work when they bridge over the sidewalk, as depicted in the Berlin examples on the previous page. Since Toronto ROW's include the sidewalk, this unfortunately wouldn't be possible here.
 
It looks like the original property line extends to the Novotel building supports on this section of the Esplanade as shown on the site plan approval drawings. This “75 The Esplanade” walkway was always a problem in the past when the previous lot owner would push the parking spots out to the limits and ground maintenance was minimal. I guess it was never a city sidewalk but they did push the properly line back a bit during this transaction.
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Colonnades only really work when they bridge over the sidewalk, as depicted in the Berlin examples on the previous page. Since Toronto ROW's include the sidewalk, this unfortunately wouldn't be possible here.

It's possible, but the city would be relinquishing property rights to the sidewalk part of the ROW, which they would be very hesitant to do. It could come up if a developer really wanted to build over the sidewalk to maximize the floor space of building. Then, I think the city could allow it provided the public realm remained high quality through the colonnade and the developer paid a lot of money.

Sometimes, though, colonnades are nice features even if they don't bridge the sidewalk. 121 King Street West has one, and it's nice to walk through the sheltered space when it's snowing. A surprising number of buildings actually have them in the city, but they rarely continue across more than one property, which limits their value.
 
@mburrrrr has done a great job posting from above. I've collected, aligned and GIFed all these aerial views for a summary of what's been done so far (might take a minute to load/play at full speed)
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