You've picked some beautiful examples of urban streetscapes. I hear what you are saying and to a certain point I agree, and I must also confess there is an element of obscure taste on my part. You make a valid point about the streetcar tracks vs. the wires - unlike the tracks, retaining overhead wires could be construed as unnecessary and nostalgic. However like it or not, Toronto is the rust-belt city that made it; it could also be construed as false to 'put on airs' so to speak, and get all gussied up in an attempt to hide our humble origins. You mention wooden sidewalks - in the urban context this is a distinctly Northern-North American frontier trait. One which (fire codes notwithstanding) people have fought to preserve.
When I first moved to Toronto 6 years ago I was astonished by how decrepit and dated parts of this city were, and how banal so much of the architecture and landscape was compared to my preconceptions and to other places I've lived. But over time, coming and going, it's these areas that have grown on me and have become most ingrained in my memory.
70 years ago cities throughout the rust belt became ashamed of their origins and began demolishing entire historic districts in hopes they could become more contemporary. The sad ending to that story was many of these places never survived because of it. I'm not saying all of Toronto needs to be gilded and turned into a museum, just that remembering where you come from is important, especially in a place as new as Canada.