"So my question is.. if we sell our house and send our possessions travelling to Canada, ready to finally start our life there, but we get to the border and he has been outside Canada over the allotted 3 years total, how do we prove to them that he has spent most of that time with me? I am worried about not convincing them enough and him potentially losing his status just when we're finally able to fully settle."
If he has a valid PR card and you arrive at a PoE in Canada TOGETHER, there is little risk of being pressed much about his compliance with the Residency Obligation. The sooner the better, of course, but as long as you are traveling together the risk of being pressed should be low.
If pressed, his and your attestations should suffice as long as you also can present your Canadian passport plus a reasonable amount of documents reflecting living together at the same residence for at least two recent years (enough to cover BOTH reaffirmation of common-law status AND, more particularly, to cover the two year RO based on accompanying a Canadian citizen spouse abroad).
The failure to make the move to Canada as planned pursuant to the sponsorship while living abroad could invite separate questions about possible misrepresentation in the sponsored application process. BUT here too, his and your attestations should suffice to explain intervening contingencies DELAYING the move. This is not likely to come up but it is possible. If the two of you are arriving together attendant relocating to Canada that should easily resolve any concerns.
"Also, the last time he was in Canada, we arrived together but he had to leave earlier than I did, so he returned to the UK alone. However I rejoined him a week later. Is it an issue that he left Canada alone? Would that mean he wasn't "accompanying" me? Or is proof of living together abroad sufficient?"
There have been SOME (not a lot, not by a big margin) reporting about the
who-accompanied-whom question coming up (there is a topic here in which this is discussed in-depth), and of course where the PR has never established any in-fact residence in Canada is one of the more obvious circumstances in which such concerns can arise. BUT so far the known cases in which this has been at issue are largely rather extreme situations, circumstances in which there is a rather obvious reason why IRCC or CBSA has concerns.
CBSA border officers are NOT likely to press or be suspicious about something like this UNLESS there is some overt reason inviting suspicion. As noted above, again, if he has a valid PR card and you arrive at a PoE in Canada TOGETHER, there is little risk of being pressed much about his compliance with the Residency Obligation. The sooner the better, of course, but as long as you are traveling together the risk of being pressed should be low. Even if pressed, his and your explanations of the overall situation should easily satisfy border officials. AND even if you run into a particularly difficult border officer who decides to make the 44(1) Report, the explanation should at least satisfy the second officer, who acts under the label "Minister's Delegate" (even though usually this is simply just another officer), that at the least H&C reasons justify retention of PR status. And even if that does not go well and there is a Departure Order issued, he will be allowed into Canada and can then appeal, and if the two of you are then settled in Canada to stay, the odds are very good the appeal will result in a favourable outcome allowing him to keep status.
The above is more opinion than I ordinarily offer. But I doubt I am going out on a limb here. That said, sure, the sooner you make the move the better. If, for example, you arrive in Canada just a couple months before his PR card expires, that puts more pressure on the CBSA officers whose job it is to enforce Canada's immigration laws, including the PR RO.
As
@canuck78 suggests, there is a POSSIBILITY your situation invites
who-accompanied-whom concerns. And there are other details which can influence this. But there is little sign Canadian officials have a strict approach to this UNLESS there are fairly blatant reasons for them to be suspicious that the immigration system is being manipulated and abused. As you have presented your situation that does not appear to be at all your situation. Additionally, the
who-accompanied-whom cases tend to arise where there is an application for a PR Travel Document . . . the fact that the two of you are arriving together to come to Canada to stay, and it is still within the first five years after his date of landing, is very different from any of the
who-accompanied-whom cases I have seen (and I watch for them).
I sponsored my common law partner and he got PR status in early 2017. We visited Canada to officially start the status within the window available and squeezed in a visit to my family at the same time. We thought we'd have the move sorted within about a year-ish, knowing that as long as he was in Canada 2 out of every 5 years it was ok so weren't rushed as we had a lot to sort out. However various circumstances have meant we didn't move as soon as we had planned (for example, his father got ill and was given a month or so to live but managed to survive, barely, for 18 months). It looks like we might not be able to move until we have gone over 3 years outside of Canada for him. However, he has lived with me, his sponsor, the entire time and we have spent very little time apart since (maybe a few weeks total where I travelled without him a few times). So my question is.. if we sell our house and send our possessions travelling to Canada, ready to finally start our life there, but we get to the border and he has been outside Canada over the allotted 3 years total, how do we prove to them that he has spent most of that time with me? I am worried about not convincing them enough and him potentially losing his status just when we're finally able to fully settle.
Also, the last time he was in Canada, we arrived together but he had to leave earlier than I did, so he returned to the UK alone. However I rejoined him a week later. Is it an issue that he left Canada alone? Would that mean he wasn't "accompanying" me? Or is proof of living together abroad sufficient? Will we have to calculate how much time we have been apart so it can be included in his record of how long he has been officially "outside Canada"?
Any advice much appreciated as I have found very little info on how this actually works in practice!