I cannot offer much other than what has already been said about the prospect of H&C relief. By the way, there are many discussions in this forum in which you can see H&C cases discussed in some depth.
I can say that at this stage it is more or less decision-time, commitment-time. The effort to save PR status may not succeed, but to have any chance of successfully keeping PR status, that will demand a more or less ALL-IN effort, a real commitment.
Additionally I think I can offer some clarity regarding procedure.
PROSPECT of PoE WAIVE-THROUGH:
Given Covid-19, and your explanation of the circumstances surrounding how long it has taken to come to Canada to settle, there is a chance that border officials will waive you and family through without going through the formal procedure attendant the issuance of a 44(1) Report for Inadmissibility, due to a failure to comply with the Residency Obligation.
I cannot guess what the chances are for being, in effect, waived through. In normal circumstances, given the length of absence, the probability of a formal 44(1) Report procedure at the PoE would be high. There are indications there is may be more leniency being exercised at the PoE, and reasonable expectations suggest this may be particularly true for PRs within their first five years.
Advantage, if this is how it goes, is that once you enter Canada you are personally in full control of whether there is any other event in which RO compliance might be examined. Thus, if you stay in Canada and avoid making any applications to IRCC, once you are in compliance with the RO your status will be secure.
The disadvantage you and others have discussed: the level of restraint precluding travel abroad for TWO years.
44(1) REPORT and ATTENDANT PROCEDURE AT PoE:
Given the length of absence, regardless of the mode of travel (by air and arriving at an airport PoE, for as long as you have a valid PR card, or travel by land via the U.S.), you are of course subject to being what many truncate to "REPORTED" upon arrival at a PoE. Being "REPORTED" refers to the procedures attendant the issuance of a 44(1) Report for Inadmissibility on the grounds of a Residency Obligation breach.
Even many who go through these procedures tend to describe it in general terms of outcome: Reported followed by being allowed to enter Canada, with thirty days to make an appeal.
That is kind of how
@IndianBos described it, but contrary to what
@IndianBos stated, if there is a 44(1) Report issued the decision at the PoE is indeed THE formal decision deciding whether PR status is terminated (revoked) or not. Even if that decision is made, to revoke or terminate PR status, and thus the PR is issued both a 44(1) Report AND a Departure Order, there is a right of appeal and otherwise that decision, or more to the point the Departure Order, does not take immediate effect.
The PR then gets to enter Canada and --
-- If the PR does not appeal, the decision to revoke PR status and Departure Order take effect in 30 days. At that point the now former PR has the status of Foreign National.
-- If the PR makes a timely appeal, the Departure Order continues to be unenforceable, not in effect, as long as the appeal is pending.
-- -- If the PR does not win the appeal, the decision made at the PoE becomes effective, the Departure Order is enforceable, and at that point individual is a Foreign National. This happens if the PR loses or abandons the appeal.
-- -- If the PR wins the appeal, the Departure Order is set aside, and the PR continues to have PR status.
NOTE regarding appeal by a PR who was in fact short of RO compliance, other than a remote chance of an appeal based on a failure to provide procedural fairness, the only grounds for winning the appeal are H&C reasons.
Disadvantage here is that to have a decent chance of winning the appeal you will need to STAY in Canada (with perhaps BRIEF trips abroad, but best chance of succeeding in the appeal is to stay) WITHOUT knowing how it will turn out, whether the effort to make a life in Canada will come to an end if the appeal is lost.
More Detail Regarding Particular Process at PoE Attendant Decision Terminating PR Status:
The process for being "Reported" upon arrival at a PoE generally goes like this (with some variation sometimes, but usually it goes like this):
-- First there is a referral to Immigration Secondary, where there is an examination involving questions related to RO compliance.
-- When the examining officer determines the PR has failed to comply with the Residency Obligation, that officer issues the 44(1) Report.
-- A second (different) officer then reviews that Report and also interviews the PR, and in doing this must consider whether there are sufficient H&C reasons for allowing the PR to keep status. This interview can be done telephonically with the second officer at a different location. (One of the variations in the process can occur if a second officer is not available, and the PR is allowed to proceed into Canada pending a later interview and review by a second officer.)
-- At the conclusion of the interview and review with the second officer, that officer (who is acting on behalf of the Minister, so is called the "Minister's Delegate") decides whether to set aside the 44(1) Report or to issue a Departure Order. That is, the second officer, usually then and there while the PR is still in airport, makes the decision whether or not to terminate PR status.
-- If the decision is to revoke PR status, the second officer issues the Departure Order to the PR, following which the PR is allowed to proceed into Canada (since the Departure Order does not become enforceable for at least 30 days).
Anecdotal reports describing this suggest that the individual going through this process might not be clearly informed about what is specifically happening. In particular, since it is common for a traveler being examined in Secondary to be talking to multiple officers, anyway, it might not be clear to the traveler when there is the formal hand-off, so to say, from the officer issuing the 44(1) Report to the second officer who also asks the traveler questions.
Bottom-line: Once the matter goes to the second officer, it is usually all about whether the H&C reasons will be enough. The second officer is the one making the decision whether or not PR status is terminated. A favourable decision by this officer, the PR is good to go (and should even be able to make a PR card application, but best to wait several months at least before doing that). A negative decision by this officer is a decision revoking PR status, which is the final decision unless the PR appeals and wins the appeal.
APPLYING FOR a PR TRAVEL DOCUMENT:
If you fail to make the trip before your PR cards expire, or you elect to wait until your PR cards expire, you can make applications for PR Travel Documents and include with the application a request, plus supporting evidence, to be given H&C relief allowing you to retain PR status.
The disadvantage in doing this is that the odds of a negative decision appear to be higher than what you are likely to encounter at a PoE. For one thing, in this process there is a specific statutory presumption that a PR abroad not in possession of a valid PR card does not have valid PR status. This does not raise the bar by much, but it does raise it some.
The advantage is you do not need to fully invest in making a trip to Canada prepared to live in Canada for two straight years. If the application is denied you can still appeal, even though these tend to be very tough decisions to win on appeal. But if the application is granted you can travel to Canada knowing you will be allowed entry without being reported and it should reflect that the decision was based on H&C reasons, so you could apply for a new PR card once in Canada. And you would not be stuck in Canada for two years (trips outside Canada should still be few and SHORT, but otherwise the PR TD application H&C decision gives you significant cover, so to say).
That is, a PR TD application allows the PR abroad a way to get a more or less clear answer, and if it is yes the PR can go to Canada without the prospect of losing an appeal hanging overhead.
