I was just reading a bit about Canadian cut glass in Swan's American Cut and Engraved Glass. Evidently they didn't have anything in the way of good blank makers, so the good cut glass made there is on American or high-quality European blanks. The cut glass industry was small, and many of the patterns were copied from American ones.
In connection with Gowans, Kent and Co. it talks a fair bit about Harry Clapperton, who moved from Stourbridge when he was 12, apprenticed with Libbey from ages 17-27, then began at Gowans, Kent in 1900; "It is said that he originated glass cutting in Canada at this firm." By 1905 he started his own firm. It doesn't say whether Gowans, Kent kept cutting after that.
Since you invited comments on the pitcher - I personally wouldn't class it with most of the other glass you've shown us. The design isn't very difficult to execute, or very inspired. Is the crosshatching polished? It doesn't appear to be. Most American cut glass aficionados would point to that alone and conclude it probably wasn't American, and I suspect they would also point to the jug as evidence for the Americans' rich cut glass superiority. BUT it's an entirely different thing seeing a piece in a single photo, and seeing it in person! I guess I just find your other pieces more interesting/impressive.
...(EDIT) I just possibly found the pattern of your jug. The general motif is called Harvard. Swan shows a few pieces by Gundy-Clapperton (where Clapperton went after Gowan, Kent) called Hob Star. Two of them have a hobstar border, but there's also a cologne shown (pg. 155) that doesn't have the border, it's all Harvard, and still called Hob Star. See Leni's thread - she has a bowl that may be the same pattern.