To follow-up . . . Another area my summary glosses over is the impact of the global pandemic. This has and will certainly continue to affect actual experiences at the border, for at least awhile. So anecdotal reporting based on this past year or so, and for the next while, is likely to be different from the historical reports (pre-Covid) and also NOT reflect how it will go in the future.
Based on what is reported in actual cases in official decisions published by the IAD and Federal Court, even without supporting personal anecdotal reports we can fairly confidently infer that for now many PRs abroad who have failed to return in time to comply with the Residency Obligation will have good odds of being allowed entry without being reported despite being in breach of the RO. There is no sign, however, that this means a universal relaxation of RO enforcement, and it is easily guessed this will more likely benefit some more than others, such as benefitting the so-called "soft-landing" PR who planned to return in Canada within a time frame that would comply with the RO but Covid interfered and delayed their move to settle here. In contrast, the PR who has been abroad five years or more, as of now, as set out in the initial query, is not so likely to benefit from Covid-related leniency in screening returning PRs. For obvious reasons: they were in breach of the RO before the global pandemic began.
There have been some reports, too few to be given a lot of weight but they could indicate current PoE practices generally, at least for awhile, suggesting minimal scrutiny for RO compliance upon arrival here, given more focus (for returning Canadians, which PRs are, as in PRs are not Foreign Nationals) on Covid-related screening. Many of those giving these anecdotal reports offer sketchy details at best, so it can be difficult to distinguish what reflects practices by border officials versus what is driven by the individual's personal situation. And, frankly, I am not paying as close attention to these because operations at the border during this period of time are undoubtedly skewered by the situation the pandemic has created. Given that IAD decisions are typically published a year or two after a PR is reported and has appealed, that source of information about actual cases is always a little dated. And the IAD, like everything else, has been especially slow during the pandemic, so that source of information will likely be little more than a trickle for awhile to come.
It warrants noting with emphasis that a lot can and often does depend on the individual's credibility and officials' impressions about the individual generally and impressions specifically considering the individual's relationship to Canada. Counting days is technical. It is mere arithmetic. And that is what the law prescribes. But it is amply clear that Canadian officials are significantly more lenient and flexible than that. Which leads to more than a little confusion because that sort of leniency and flexibility tends to be unevenly applied. So the anecdotal reporting shows this and that PR being waived into Canada despite being in breach of the RO by many months or even a year or more, but then other anecdotal reporting shows some PRs being Reported for similar or even significantly smaller breaches of the RO. Some here might accuse the officers of discrimination or being arbitrary. Some say this is random. And there is probably some of that, but just some. The more likely explanation is rooted in the manner in which discretion is exercised, the broader the discretion the more widely disparate the outcomes, and this is aggravated significantly the more subjective the discretion. Does not mean the decision making is discriminatory, arbitrary, or random, but that the criteria varies and is prone to more subjective variation.
Which is why seasoned forum participants will caution that any PR in breach of the RO is AT-RISK of being Reported upon arrival at the PoE, and few will attempt to quantify the risks, or to speculate much about the precise probabilities or odds. The obvious is, of course, obvious: the longer the PR has been abroad and the more in breach of the RO, the greater the risk the PR will be Reported upon arrival at the PoE.