As someone born in Toronto, the weather is crap. You're right by a great lake, so it's damp/humid all year (step out of the shower and start sweating humid). Downtown is a series of giant wind tunnels, which isn't bad in the summer, but is downright chilly in the winter.
I moved to Calgary and the weather is great, nice and dry and Chinooks to warm you up during the winter.
I guess weather preferences are subjective. My wife prefers TO weather over SF weather. Her reasoning is that TO has "real seasons". I used to live in Sao Paulo. Great weather IMHO, if you're ok w/ 38C in summer. SF weather feels chilly all throughout the year IMHO. The weather inland in the Bay Area tends to be much better for my taste. YMMV.
I moved to Calgary and the weather is great, nice and dry and Chinooks to warm you up during the winter.
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