Thanks for interest in my post, sstanger1.

As far as I know, there were no family connections to bring Demsey to Canada, whatsoever. He showed up on the 1916 census in Benson, Saskatchewan as a Farmer & Head of Household with 1 older man (unrelated) working for him. He was not married before or after emigrating to Canada, as far as I can tell. He was not in the military either (although I did find his United States WW1 Draft Registration info).

So after the 1916 Canadian Census, the next instance I find of him is in 1930; he shows up on the U.S Census in El Dorado County, CA as a Logger.

Regarding border crossings: The only border crossing I've found (so far) is for Demsey's father (my great grandfather who lived in Bottineau County, ND) to Edmonton in 1919 and he was carrying $1100 with him. I don't know what that would've been for. That's a mystery, too!