If I might expand on my previous post bit, there are things that I would say Toronto does particularly well:
- Successful, progressive planning. This can be seen in the dense, seamless downtown, dense suburbs, greenbelt, the prevalence multi-family development throughout the city, high-transit usage, neighbourhood redevelopments, and continued pace of development of all types (housing, offices, institutions, transit, parks, street improvements), while all being quite "livable". Plus we aren't plagued with over-powered NIMBY groups.
- Vibrant summer street life and finely scaled neighbourhoods. Best exemplified by Victorian "village" centres like Kensington, Baldwin Village, Yorkville, etc; and of course the patios, sidewalk markets, festivals, beach parties, and old high streets. Laid-back urban funk. I know this is supposed to be Montreal's thing, at least within Canada, but I think Toronto does it just as well - each just with their own unique take on it.
- Diversity. And it's not just ethnic diversity or neighbourhood diversity either. There is always a huge range of and a lot of "stuff" going on. Like, any sort of subculture or music scene or trend or whatever however niche will have a following in Toronto. The built form itself is quite diverse as well, with just about every North American urban archetype existing here.
- The presence of nature within the city. From the mature tree canopy, to the ravines, beaches, rivers, the lake, and the overgrown, ivy covered buildings, to the raccoons scampering about - it's ubiquitous and well integrated with the urbanity.
Meanwhile, ways in which the city performs particularly poorly:
- The often tawdry state of the public realm. Wood utility poles, patchy concrete, cheap sidewalks, decrepit infrastructure, that sort of thing. It can sometimes be charming in an endearingly trashy way, but mostly it's embarrassing.
- Ugly-ass suburbs. I guess this is a problem for most cities in North America, but still, they seem particularly dreary and depressing here.
- Congestion. Between transit expansion not having kept pace with usage and population growth, roads never having been built to handle the capacity that they now do, and a poorly thought-out system of bike lanes, getting around the city can be a grueling experience.
- Outward-looking culture. This is something that effects most of Canada, but is nonetheless a regrettable situation as most Torontonians are viewing their own culture through an American lens (and of course, everything American is "better"), rather than actively participating in and fostering what is uniquely ours.
- Politics. This goes well beyond Rob Ford (and other lunatics like Giorgio Mammolitti and Doug Ford), to a quarrelsome & paternalistic city council, and an overbearing bureaucracy governing the city. As well, decades of mismanagement at the provincial level - and in particular, having the issue of transit expansion being played as political football have left the city's infrastructure in a mess. Of course, I can't just blame the politicians themselves - they exist because there are a whole bunch of people who support 'em.