I'm getting sick of people blaming the city, so I'll say this again.
The city had literally no option to give UBER a go ahead. There are provincial rules, discussed over and over again. The city cannot endorse a company that does not follow those rules. Should those rules be tweaked? Perhaps, but the city cannot tweak them, they are bound by the provinces rules.
The way the city has responded to the whole thing is they only way they legally could have responded.
I suspect very early in negotiations between uber and the city, the city would have told them, "ensure your drivers all have the proper licences and insurance, and then we'll talk. Without that, we cannot possibly endorse you". To which uber likely said "that's not part of our business model." All the city can do at that point is try to work with the province to tweak the rules - but in general, those rules are there for a reason.
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