Weeeeeellll, if you really want to bike year round, you need to go to Vancouver rather than Toronto because although it rains a lot in Vancouver, Toronto is much colder and has a lot of snow.
Here's a link to Vancouver weather and climate info.
http://www.theweathernetwork.com/weather/CABC0308
Vancouver hovers around zero in the dead of winter, probably between 1-10C in the day and below freezing in the night in parts of Dec/Jan. If you have fenders and don't mind rain, you can ride most days.
Vancouver is a big city so there a lots of races around, plus you can always pop into the Okanagan and do the Apple Tri in Kelowna or the IM in Penticton. PM Grog and she can probably tell you lots about cycling races in Vancouver. Plus you can google it too.
Vancouver is also expensive for accommodation - google rental prices to get an idea. Of course, you don't have to live right IN Vancouver, the suburbs are slightly cheaper and often safer. Burnaby, Coquitlam, Surry, North Delta, Richmond... Some are more expensive than others.
What are planning to do for work? That would be a big determinant for where you want to live. There is a pretty good bus system and light rapid transit in much of the greater Van. area too.
There's a starbucks and an indoor ice rink on every corner.This IS Canada eh...
I'll go look at my last grocery bill and get back to you on food prices.



This IS Canada eh...
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