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BeShoo said:
Thanks for the clarification. I think I understand it much better now. I guess we'll take our changes with another visitor extension. Received wisdom is that every extension is less and less likely to be approved, but the last extensions we've received give something like "complied with all conditions" as the reason for the extension.

I would request the extension and if its granted proceed as normal with the outland application through CPP-Ottawa... but if it's rejected then get an inland application in asap so he can get implied status and stay here.
 
Thanks to your advice, I've decided that outland is the way to go. I haven't applied yet for an extension to the Visitor Record which expires January 10. We haven't sent the PR application yet, either, but I'd like to do that by Monday.

We did go to Pennsylvania last weekend and returned Tuesday morning just after midnight. The border checkpoint was completely deserted except for one officer in a booth. There were no other cars going through. Despite the fact that the CBSA officer didn't appear to have anything else to do, he didn't ask many questions. He asked where we lived and where we'd been and what we were bringing back (specifically if we had firearms). He unfolded and folded the Visitor Record in the passport twice and asked if we both live in Gatineau, then he sent us on our way.

It occurred to be that this ought to be considered a new visit to Canada, starting last Tuesday, and since there were no stamps put in the passport, shouldn't it be implied that he has 6 months for this visit or does the expiry of the VR take precedence over that? I'm wondering if I have to request an extension right away or if I can wait until closer to June. Does anyone have experience with that?