Couple more things though, At the port of entry do they check every person's RO eligibility or is it done based on random selection or in case any doubt is raised while asking basic questions such as how long you were out, purpose of visit etc?
Also, my wife and my older child will not be in breach of RO since they have not left Canada since we moved here in Feb 2021. Also, my second child is Canadian citizen. Does they traveling with me increase my odds of being waived through?
While I largely agree with
@armoured's observations, it is safe to say that the vast majority of times a PR arrives at a PoE returning to Canada there is NO particular screening of the PR's compliance with the Residency Obligation.
I traveled frequently, and just as other PRs I have known personally have said, and this is consistent with forum and other sources of anecdotal reporting, there were never any questions even remotely about RO compliance . . . except, what most returning Canadians are asked, in one way or another, as to how long you have been abroad, which is asked for customs' reasons as much as immigration, but which may signal factors potentially leading to questions about RO compliance. Obviously, a very lengthy absence in itself can suggest cause for RO compliance inquiry, and especially if the absence approaches three years, noting that an absence of three years or more is on its face an indication of a RO breach (unless the PR is entitled to credit under one of the exceptions, which it is the PR's burden to present and prove).
Beyond that, as
@armoured alluded, there can be a range of factors that invite more specifically RO related questions, and as
@armoured specifically referenced, some PRs are "flagged," meaning there is an "alert" on their GCMS file that pops up when a border official pulls up that PR on their computer.
A big clue that a particular PR might be asked more questions about RO compliance is having been asked RO related questions during a previous PoE examination. It appears you have arrived here from abroad more recently than me (I have yet to travel abroad since covid), and you know how it went during your PoE arrival experience, so you could be providing some anecdotal insight into the extent to which you have encountered RO related questioning. Again, if you have already been asked questions about RO compliance, yeah, that's a clue you will be examined more thoroughly about this when you next return to Canada.
There is such a wide range of information that PoE officials can see, if they look, and much variability in terms of what they look for, as
@armoured also suggested, trying to forecast the nature and extent of questions a particular PR will encounter is indeed speculative.
Basically a PR who is
cutting-it-close, and especially any PR who is in breach, should anticipate being questioned, and be prepared to give SIMPLE, STRAIGHT, HONEST answers, and if in breach, prepared to offer a BRIEF explanation of the reasons for the extent of absences (and as previously noted, where a medical H&C factor is involved, have IN HAND some medical records to show, supporting the explanation -- but still keep it as simple as possible).
And note: they can, and sometimes will access your CBSA travel history. While it was prior to me becoming a PR, and thus not RO related but length of stay in Canada related, they were able to do this and for me did it fifteen years ago; and their record capturing, and access, has been much expanded and improved since then. The PIL officer may not look, but they can, and if referred to Secondary the likelihood increases border officials will access details of your travel history; ASSUME they know the truth.
There are generally very low odds of playing the system, that is other than minimizing the extent to which one is abroad. So, for example, whether to be traveling with family or not should not be influenced based on how it might affect your examination upon your return. PoE examinations simply vary so widely there is no reliable way to script or orchestrate things, and just attempting to do so can be and often is far more transparent than many realize (contrary to many opinions in forums like this, border officials tend to get it, they tend to know far more than many give them credit; they have screened thousands of travelers, after all, and learned some things along the way). Straight, simple, and honest tends to work the best. (Sure, there is no shortage of those skilled in the con and they can be particularly able in pulling the con off . . . so many
get-away-with-it, so to say . . . but many more don't, and many way overestimate their abilities in this area, and if and when border officials get the scent
someone-is-gaming, that can be, well, a
game-changer, as in NOT good.)