Hey guys,
I have the same question because my visa will be expired before my landing. I plan to do two things separately. First, I will complete the landing, keeping my I-94 attached to the passport and I will be back to US less than 30 days with AVR. Then I'm going back to can to get the new US visa, it shouldn't be more difficult in Can than your home country. My friend get his US visa in Can twice (he got multi-entry tourist Visa to Can) without any difficulties.
Anyway, I just want to point out that we shouldn't mix thing up, finish the task one by one. We are not the only ones, there are thousand and thousand of similar situations happened before I guess
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Per AvayaLenovo list of items. I guess I will bring cash + traveler check on my first landing to open bank account, credit card and SIN, insurance etc. Then I will come back to US to put my asset on liquidation, then move myself to Can on the REAL landing
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Keep on brainstorming, I'm glad to share my thoughts here.