I believe Uber launched in Edmonton in December 2014, by September 2015 it had a proposed bylaw ready - of course with it's own rough patches. Neither the taxis or Uber were thrilled with the proposal, but it was clear that in Edmonton progress was being made and there was some headway less than a year after it's first introduction into the city.
Uber first launched in Calgary, as a limousine service, in October 2013. More than a year later, in November 2014, Nenshi was calling Uber jerks. Another year after that and the city had no proposal regarding UberX, rejected a proposal with regards to Uber Black, had an undercover sting operation to fine drivers and trying to approve an injunction to arrest Uber drivers.
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