Residency Obligation While in the US ?

[uncomfortable]

It doesn't matter actually. It was observed multiple times that travels to the US and mere having US visa triggers RQ often. With the way of life OP thinks about RQ will be almost inevitable.

I envy your certainties considering how variable this whole matter is. Reality is we don't know what is going to happen, so I wouldn't be as categorical. Chances are it will take longer for him to go through the process, but considering that he will have an i-94 and all the entry records into Canada (and I would strongly encourage him to obtain a NEXUS Card), with a well-kept travel record he should be ok.

 

[CanadaSimple]

We can never say that everything will be ok. But in some situations, we can with a high degree of accuracy predict that the process won't be fast and simple.