[Architype]

So, I'll try again from the beginning:

Most Canadian:
1 Winnipeg - central, has stereotypical Canadian climate, seems typical and average for a Canadian city
2 Ottawa - because the capital must define the country
3 Halifax - represents importance in early Canadian history, seems representative of typical eastern Canadian culture.

Least Canadian:
1 St. John's - because it has it's own more distinct culture, and was not part of Canada until 1949
2 Montreal - It is important, but is not generally thought of as typical Canadian for obvious reasons
3 Victoria - same as before, it's more remote than Vancouver, the climate is milder than what is typical Canadan, it is strategically positioned for NW American influence.