Great question — answering as the UphillTech team:
We now see that a Canadian transit visa only allows two entries: Correct. It can be one or two entries, so you would need (at least) 2 transit Visas What's the likelihood that we can get two Canadian transit visas? Not much different than a single one. It's for the same purpose for the same person with the background. You might get a little extra scrutiny because of the odd itinerary but "trying to avoid US immigration at the moment", is a a valid reason that Canadian immigration is quite likely aware of. we should apply for a temporary residence visa instead of a transit visa, but surely that's overkill Maybe not. It's just a fancy name for the "normal" Canadian tourist visa. If you think,...
Full answer by Hilmar: https://travel.stackexchange.com/a/203230 (CC BY-SA 4.0).
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