Originally Posted by FrAnKs
Your own criterias.
Then I'm going to take the easy route and cancel out all aspects of my personal situation other than my personal tastes in cities. I'm going to assume the same income, adjusted for the cost of living in the various cities combined with a travel top-up for more distant cities to cancel out the benefit of family proximity. I'm also going to assume I'm commuting to my workplace across a proportional distance (let's say, across 1/2 the radius of the metro area, although this is awkward given the non-circular nature of some). I'm also canceling out linguistics, because not being fully bilingual would be a challenge in some cities, but that's a characteristic of me rather than the cities.
1.) Montreal. I find the built form the most interesting and engaging, I love the energy, culture, history, and the charisma. And also the bicycle and public transit activity. Downside: wintertime cold and snow, horrible suburban morphology.
2.) Vancouver. I love that it's mild, that it's dense, I love the architecture of the eastern parts of the central city, the progressiveness, the proximity to nature, and the decent size. Downside: rain
3.) Victoria. Mild temperatures, colourful city centre, outdoor recreation opportunities, attractive setting. Downside: Size
4.) Halifax. Progressive, local culture, setting, history/built form, uniqueness, options for day and weekend trips in the region. Downside: Small
5.) Saint John/ St. John's (tie). Built form, setting, history, uniqueness, strong sense of place. Downside: Small
Runner up: QC. Impressive built form and density, especially given its size. Beautiful setting.