Given the good and thorough commentary by
@armoured, and the clear statement of your options by
@Besram Tuesday, as well as clear responses by
@Naturgrl, not sure much more needs to be said.
But I will offer some observations about the procedure.
There are three main reasons why the odds are better arriving at the border from the U.S., in contrast to applying for a PR Travel Document:
2) The primary focus of screening a returning Canadian at a Port-of-Entry is to verify their Canadian status (PR or citizen), and thus a returning PR might not even be asked questions about their compliance with the RO; in contrast, an application for a PR TD requires the visa office to make a Residency Determination, and the PR must include sufficient information and some supporting documents to facilitate the visa office in making a determination the PR has complied with the RO
3) The PR arriving at the border via the U.S. will be allowed to enter Canada even if issued a Removal Order, and this will allow the PR to remain in Canada pending an appeal . . . while staying in Canada pending an appeal may only improve the odds of succeeding by a little, being outside Canada while an appeal is pending hurts the odds considerably
That is, there is very little chance of a lenient waive through the PR TD process.
In contrast, there is a real chance of being waived through a PoE without being subject to a more or less formal Residency Determination. And even if an inadmissibility report is prepared, and the officer reviewing that report is not favourably persuaded by H&C factors, so a Removal Order is issued, the PR still gets to enter Canada and stay pending an appeal (notice of appeal needs to be filed within 30 days; appeals generally take at least six or more months, often a year, sometimes much longer such as it was in the wake of Covid).
. . . "if the agent is hostile, he will start a 44(1) . . . "
Notwithstanding occasional claims to the contrary, even when dealing with difficult clients,
generally CBSA officers are NOT hostile. It happens, sure. They are human. Flawed. Prone to some biases. But mostly, and mostly by a big margin, they are professional and courteous.
They are nonetheless law enforcement officers (employed by the Department of Public Safety) with a mandate to apply and enforce the law. If a traveler with Canadian PR status is referred to Secondary, and in the examination in Secondary the officer determines the PR is in breach of the PR Residency Obligation, it is the examining officer's duty to prepare a 44(1) inadmissibility report. That report is then and there, while the PR is still in the Port-of-Entry (thus not yet given permission to enter Canada), referred to a second CBSA immigration officer whose job will be to review the report, and if the report is valid in law (which, if you have not been in Canada at all for more than the last three years, the breach is obvious) then assess whether you should be allowed relief, allowed to keep PR status, based on H&C reasons. None of the officers engaged with during this process are likely to be "
hostile," but doing their job.
Some are undoubtedly more lenient than others. But again, none are likely to be hostile.
Among the reasons it is said that the odds are better arriving at the border from the U.S., in contrast to applying for a PR Travel Document, is that anecdotal reporting indicates that a significant number of PRs in similar circumstances are waived through the Primary Inspection Line, no referral for examination in Secondary. The outcome of that is the PR is allowed into Canada without being subject to inadmissibility proceedings. If this happens, and the PR can stay for two years, that will cure the RO breach, and the PR gets to keep PR status.
Even if referred to Secondary, anecdotal reporting suggests that some PRs in RO breach are waived into Canada without an inadmissibility Report being prepared. Despite clearly being in breach of the RO. Why varies, ranging from officers too busy to bother, to others just plain being lenient, or it may be due to the Secondary officer being sympathetic to proffered H&C reasons (technically this is not the officer whose job it is to assess whether there are sufficient H&C reasons to allow the PR to keep status despite the breach).
Making the H&C case:
That's a big, complex subject. For PRs who are in breach by a lot (more than a year), making the H&C case is tricky. I fully concur in the approach suggested by
@armoured . . . focus on explaining YOUR reasons for not returning to Canada sooner, YOUR STORY so to say. If that does not work at the PoE and you need to appeal, you can (and in my view you SHOULD) get a lawyer to help make the H&C case on appeal.
Thing is, as noted, making the H&C case is tricky. Employment related issues and reasons, for example, can have a positive influence in some cases, or have no influence one way or the other in a lot of cases, or be a negative factor in the assessment of H&C reasons. Most people can effectively tell their story, the way it is, and come across more honest and genuine doing so, and during a PoE examination that is hugely important. (To the extent there is a risk of triggering a border officer's hostility, being evasive let alone appearing to hide something will increase the risk considerably), If need be, if it becomes necessary to appeal, again once in Canada the PR can get a lawyer's help in better making the H&C case.
Odds of Keeping PR Status:
It is impossible to say what the odds are. It is particularly difficult to assess the odds of a H&C case succeeding. However, probably prudent to caution that if it has been nearly five years, let alone more since you were last in Canada, unless you are lucky in being waived through without being questioned about RO compliance, saving your PR status is probably a long shot, long enough anyway you should be prepared for losing status . . . depending of course on what H&C reasons you have.