I too am a northern blood. I am thinking 6 months in Canada. I kind of like St. Louis, maybe for the late fall then off to the south east for the winter and early spring. Great question, I will check back.

The reason for St. Louis is that the Katy trail is close and if you want you can ride some hills nearby. I have always had a great time there, and housing is cheap, food is good and it seems close to the rest of the south and south east.