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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.
 
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?
Ah, yes, that makes sense and is completely clear now.
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).
At a certain point you are likely to get reported if you cross the border frequently and don’t meet RO.
Well, it can't happen for the next year or so. It's only once a person is below 730 days that there is a risk of a report. So there's some time before you (the OP) have to worry about this.
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.

I don't have a Nexus pass but as a PR I've been able to use my US passport to get into Canada w/o any trouble. The details are linked, and as per https://www.canada.ca/en/immigratio...ervices/canadian-passports/passport-tips.html the passport details need to be updated for a Nexus card to remain valid. So... they can probably look up the passport from the Nexus pass/card, and then look up the PR from the passport.

Thus I fully expect that they can connect the dots and using Nexus alone would make no difference.
Yes, that would be my plan to sponsor him once I'm there permanently...
If you are not compliant with your RO that creates potential issues sponsoring him.
In fact I'd be concerned attempting to raise a sponsorship application with IRCC for the child while not compliant with RO would cause IRCC to investigate and eventually attempt to revoke the PR.

Meaning that in the best case scenario, playing it safe means either living away from the child for two years while working towards RO compliance or else having the child enter as a visitor to Canada with all that entails.
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?
Your child is the one who would enter as a visitor.
Yes, exactly. It doesn't apply to you (the OP) but to your child, and sponsorship while not complying with RO is also troublesome.

You mentioned that a difficult childbirth was a reason to not move initially. This is a bit ironic as if you had moved before giving birth then the child would be born in Canada as a Canadian citizen (as well as a US citizen born overseas incidentally I'm presuming), so the concerns about sponsorship wouldn't have been an issue.

Furthermore, although it's currently closed, there's a program to allow adult children to sponsor their parents for PR in Canada, https://www.canada.ca/en/immigratio...sponsorship/sponsor-parents-grandparents.html - so having a Canadian citizen child might have given you a way to get your PR back eventually if you ended up losing it at some point.
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.

This is the worst case combination, you're not able to move back but frequently crossing the border. Odds are against you as you'd only have to get unlucky once to lose PR.

How far do you live from the border, and if it's too far to drive on a daily basis would relocating closer be an option? As per https://stepstojustice.ca/glossary/residency-obligation/ part of a day spent in Canada counts as a day in Canada for RO purposes, so if (for the days you aren't actually working in Canada but living in the US) you were still able to drive into Canada everyday for the next two years (or even just walk across and through the port of entry if you are close enough), then you'd actually be able to meet your RO.

In fact, if you're able to pull that off for three years instead of two (over 1095 days), you'd not only meet RO but might be eligible to apply for citizenship.

But there's something about this I didn't understand. You have PR and are frequently traveling to Canada for work, but you can't actually move for maybe 15 years? 2 to 15 is a large range, I'm at a loss to understand why it's potentially that long.

In fact, I didn't get why you can't move within the next year. It makes sense that you needed to give your kid some time to settle down but I'm guessing that kid will be a talkative toddler next year - a good age for such a move - and a year is plenty of time to wrap up whatever other small lose ends you might have.