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I'm a bit confused here - you say you're approaching the 3 year mark - which I take to mean something like 1095 days out of Canada), but also that it's not adding up to 730 days. I'm guessing you're a new PR still within the first five years of PR holding - so if you return to Canada now then it could indeed still add up to 730 days.
Yes, I'm in the first 5 years of having PR, so if I moved today, it would add up to 730 before the card expiration. But in the next year or so I'll be at the 2 years left mark. Does that make sense? The questions at the border are just in the "warning" phase, where they remind me plainly about my residency obligation. I am bilingual and do my best to explain to the customs officer why I've been delayed moving there permanently. They let me pass but I'm anticipating one day the dreaded 44(1) report that others speak of happening to me. If I continue to not fulfill my obligation and continue to go to Canada only for brief work and travel. (I'm going about every summer for the whole 2 months as I am a teacher, and I sometimes teach in summer programs there).
It's definitely luck of the draw. But for US citizens (which may apply to OP, who states that she is "from" the US), it seems there's actually not much difference between a land border crossing and using a US passport to get to immigration in a Canadian airport, as per https://www.canadavisa.com/canada-i...tions-is-rejected.871032/page-2#post-11059579 - rather it's applying for a PRTD where we see folks getting less lucky.
I have a Nexus pass and sometimes I only show that, but it's in my file that I'm a Canada PR. Would showing only my US passport and making no mention of my PR make a difference? I can't believe the border wouldn't connect the dots.
Yep - likely they'll just let the child in. Then, if the OP returned in time to meet RO or the OP got in via H&C, the child's PR sponsorship can be started from inside of Canada.

If the OP makes it in without being reported but also without meeting RO for a significant period of time - longer than six months - I suppose it gets trickier. Ideally OP would be able to stay two years and then apply for a new PR card after meeting a new 730 days from scratch, but a US citizen only gets six months max as a visitor.
Yes, that would be my plan to sponsor him once I'm there permanently... I just don't know if that will be in 2 years or in 15 years when I'd be able to do that. Especially with my frequent travel and work there. Would love to get lucky during all of those crossings, sigh.

I'd definitely stay the 2 years (from scratch) and apply to renew and fingers crossed. But your point about 6 months for US citizens doesn't really apply, because if I could get in to the border without a report, I'd technically still have my status as a PR (and I wouldn't be consider a visitor). Right?
 
Yes, I'm in the first 5 years of having PR, so if I moved today, it would add up to 730 before the card expiration. But in the next year or so I'll be at the 2 years left mark. Does that make sense? The questions at the border are just in the "warning" phase, where they remind me plainly about my residency obligation. I am bilingual and do my best to explain to the customs officer why I've been delayed moving there permanently. They let me pass but I'm anticipating one day the dreaded 44(1) report that others speak of happening to me. If I continue to not fulfill my obligation and continue to go to Canada only for brief work and travel. (I'm going about every summer for the whole 2 months as I am a teacher, and I sometimes teach in summer programs there).

I have a Nexus pass and sometimes I only show that, but it's in my file that I'm a Canada PR. Would showing only my US passport and making no mention of my PR make a difference? I can't believe the border wouldn't connect the dots.

Yes, that would be my plan to sponsor him once I'm there permanently... I just don't know if that will be in 2 years or in 15 years when I'd be able to do that. Especially with my frequent travel and work there. Would love to get lucky during all of those crossings, sigh.

I'd definitely stay the 2 years (from scratch) and apply to renew and fingers crossed. But your point about 6 months for US citizens doesn't really apply, because if I could get in to the border without a report, I'd technically still have my status as a PR (and I wouldn't be consider a visitor). Right?

At a certain point you are likely to get reported if you cross the border frequently and don’t meet RO. Your child is the one who would enter as a visitor. If you are not compliant with your RO that creates potential issues sponsoring him. As a visitor they are not entitled to many services. You really need to decide either to commit to Canada for 2 years or find another potential way to work for the summers in Canada expecting that you will eventually lose your PR. You also won’t qualify for health insurance if you only work for the summer so both you and your child should purchase private insurance.