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Here is a CBC article about insurance rates driving snow clearing contractors out of business as follow up and interest to people to show how seemingly unrelated issues effect our streetscape and built environment:

https://www.cbc.ca/amp/1.5818604

I know a couple of folks in the game and they say the same thing. One has completely given up working in urban areas. In small-lot residential areas, if he put snow on municipal property, bylaw fined him and if he worked commercial jobs the insurance killed him. Most residential customers don't ask about insurance and suburban/rural properties have more space to push snow.
 
This may be an odd fit for this thread.

I'm going to complain about something that arguably looks nice.

Its just the wrong kind of nice for the spot!

I was out on a walk today at was walking through the west side of St. George campus at the U of T.

As I'm walking down Huron.............I notice some pedestrian lighting.........and it just makes go............huh?

So first, I see these heritage-style lights here, between New College and the Recreation Centre.

So I ask myself...............one building screams 1960s............the other screams 1950s................who exactly thought 19th Century lighting would be a good match?

There isn't one building here, nor any other context that calls for this lighting type.

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Then I see the same lighting by McClennan Physical Labs.......

Uhhh.......how does that go here either?

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The entire length of Glen Cedar Road (especially between Eglinton Avenue and Ava Road in Cedarvale) is so worn down, it's hard to bike on it.

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This is a screenshot from October 2020. I have biked down this road recently and it's still dilapidated.
 
The entire length of Glen Cedar Road (especially between Eglinton Avenue and Ava Road in Cedarvale) is so worn down, it's hard to bike on it.

View attachment 315738

This is a screenshot from October 2020. I have biked down this road recently and it's still dilapidated.

I'm surprised that a barrage of complaints haven't led to a fix, especially in toney North Toronto.
 
I'm surprised that a barrage of complaints haven't led to a fix, especially in toney North Toronto.
Even the most affluent neighbourhood has plenty of shabby street conditions, so shabby that it is hazardous to drive or bike on the streets during inclement weather. Sidewalk conditions are no better, complete with uneven slabs, cracked slabs, deep footprints, and vegetation growing within the cracks. It's an unfortunate fact of life.

Even submitting multiple complaints from many different residents using 311 lead to nothing being done. It had to take a serious injury or death resulting from poor conditions for there to be a response.
 
UT's own @ShonTron has a piece up at Spacing looking into the fiasco of Cobra head streetlights grafted on the deco-style curved brackets of the acorn-fixture.

 
In what may be a first.........Councillor Holyday has been caught making a worthwhile motion at Council!

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From the background:

The reduced service levels have resulted in a state of disrepair for many of our traffic islands, centre medians and parkettes. In some cases the City fails to meet the property standards expected of residents, or creates situations where the integrity of the plant materials are degraded due to aggressive cuts spaced too far apart.

Visual comparison of these locations using a tool like Google Street View confirm what the neighbours have observed over time, deteriorated conditions over the years which detract from the beauty and enjoyment of our streets.
 
In the past, all permanent repairs to utility cuts were made by a City contractor and then charged back to the utility companies. Clearly there was a huge bureaucracy involved and it was VERY slow. The City is now allowing utility companies to permanently repair their own cuts and, in at least the St Lawrence area, this appears to be having some success in getting cuts permanently repaired more promptly. There are currently companies repairing Toronto Hydro, Enbridge and Toronto Water cuts and it appears (from the locates) that a Bell contractor may be about to start too. Of course, when a street has cuts made by 5 different utilities it will mean that there are 5 companies doing repairs but .... I assume that if a company does not hire a permanent repair company the City will continue to do them. I guess we will see.
 
A candidate for rustiest street sign in Toronto; taken on my walk yesterday:

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