I have a friend who works for the city whose job it is to help coordinate many utilities and other companies on the projects discussed above. To hear him describe it, it's the city that's overworked and understaffed, and his description of the kinds of people he has to deal with are, to say the least, not flattering. He used the term "suburban hicks" as virtually everyone he deals with, from senior people in the city's transportation department, through to liaison staff with Enbridge, Toronto Hydro, Aecon, etc. all live well outside the city, and could not give a rat's ass about the aesthetic concerns being discussed here.
And did anyone catch Toronto Hydro's self-congratulatory agit-prop section in the Star? I thought it was a parody, to be honest. Toronto Hydro: 100 years of making Toronto look like other cities from 100 years ago.