In others words I'm not sure just who is going to advocate for these changes: 1) the vast general public simply doesn't care or take pride in these things the way they do in other cities and 2) in the vacuum of this public apathy civic spending has been politicized and co-opted by influential, vocal interest groups that simply do not care about ugly streetscapes, and who through propaganda make it a matter of questionable 'ethics/priorities' if you do to the point where it involves money (volunteer all you want but don't expect funding while there is a homeless person on the street).
... and is this really all that different from other civic portfolios? Transit and infrastructure have also been ignored for decades because nobody wanted to spend the money or take responsibility for spending it, and consequently nothing much was done for many years. Once again, the public didn't care and there were more politically expedient ways to direct funds. Now all of a sudden (so to speak) we seem to care a great deal about mass transit, as we all know.
At the end of the day who's to say what it will take to change the public attitude towards the public realm? In fact, as has already been demonstrated by Grimace and others, we are starting to see some change. Perhaps as the demographics of downtown change as driven by mass development and the condo boom we are seeing a change in expectations that will only continue to generate momentum. More and more people want to live downtown but want to live in relatively clean, welcoming and uplifting environments. At some point the expectations and influence of this growing demographic will begin to challenge other political forces.