A brief rebuttal of some of the points:
I have never had an issue drinking in Trinity Bellwoods or High Park. As long as you are respectful and don't flaunt it there never seems to be an issue. I'm not sure I want to live in a city where the homeless are harassed by police. Where are they supposed to go if not a public park? Park maintenance seems to be better than it was a decade ago but maybe that's just me.
Kensington is already incredibly pedestrian friendly. While I wouldn't be opposed to expanding the car free sundays program I'm not sure it's really needed. It's incredibly difficult to drive in kensington as it is and pedestrians truly do have the right of way - there isn't another neighbourhood in Toronto you see people walking down the middle of the street without a care. It's also good to remember that Kensington does actually have real businesses that require things like deliveries and need to ship things out. On weekends too, even. Pedestrian only zones have a habit of becoming either sterile or very high-end. Not saying there aren't other areas in Toronto where pedestrian only zones could work well.
I'm not a huge fan of Liberty Village, although mainly from a design perspective and not a density one (it's nowhere near HK density, or even Saint Jamestown…). It's weird that people blame city planning though. I think this is a general failure of understanding the planning process and the policy framework in Ontario. There probably should have been a more robust secondary plan in place, but the greedy developers trope gets a bit old. They wouldn't build it if people didn't buy it. I actually have zero problem with Cityplace and speaking as a planner will defend many (but not all) of the decisions made there.
Not sure where else you have lived? I have been to many cities in North America that have equal if not more advertising than Toronto. Ontario is actually very good at restricting roadside billboards compared to the US.
That's an odd observation - I often find the opposite. Torontonians tend to be far too self-depricating too the point of being frustrating. When people hype up the city it's often in response to this I think. I'm ok with it because I'm sick of people claiming everything here is the "worst in the world" with zero grounding. Again, many other cities I have been too are far more boosterish in their attitude. Calgary, Vancouver and Chicago come to mind, and of course NYC (rightfully so in this case).
Again, where else have you lived? Toronto is a big city and unfortunately homelessness is going to happen. All in all I find the homeless in Toronto relatively tame compared to other places. Ever been to Vancouver, or if you really want to ramp it up a notch San Francisco? FYI a lot of homeless have dogs for security reasons. If you are sleeping rough it helps. I used to hate on it too but have had it explained to me and kind of get it now.
Why exactly? It's easy to hate on the Gardiner but it's not the real barrier to the lake. I think it is an important artery (mainly for freight reasons) and it does keep traffic off of surface streets. I'm familiar with the induced demand / teardown argument but I'm not sure it applies here. Happy to elaborate on that. There are plenty of creative options for keeping the Gardiner as an artery and making the space more attractive.
On the flip side the island airport is an important piece of infrastructure that is a major economic boon to the downtown. I don't see what the removal would gain really - we have lots of waterfront parkland. I may get flack for this but I think the waterfront is the least interesting part of Chicago. Sure it's pretty, but it's sterile and a tourist trap. After spending 30 mins biking there I was bored and went back inland where actual interesting neighbourhoods are. Also the C series jets are quieter than turboprops… I'd be fine without the expansion though.