I wouldn't include Alberta or Saskatchewan in the "docile, timid" category. Conversely, I wouldn't include Boston in the "brash, risk-taking" category. Migratory patterns do seem to tell the tale. Does it hold in every instance? No, there are always exceptions. New Hampshire seems to have held on to some semblance of the spirit of the American Revolution.
Saskatcheswan is leftist. They elect the explicitly socialist New Democratic Party to government.
From the perspective of urban Ontaio such as Toronto or Windsor even the Kremlin on the Hudson or Taxachusetts are frighteningly conservative.