Heads-up I: anecdotal reports of personal experience returning to Canada by PRs in breach of the Residency Obligation range very widely, from PRs who were simply waived into Canada with NO particular examination as to their compliance (or, more to the point, lack of compliance) to those issued a 44(1) Report for Inadmissibility due to the breach of the RO and a Departure Order. Those reports, those experiences, offer very, very little insight into what will for-sure happen when you arrive at a PoE coming to Canada, except to illustrate WHAT COULD HAPPEN. That is, anecdotal reports from other PRs in a similar situation indicate something about how it MIGHT go for you BUT do NOT indicate how it WILL GO.
Heads-up II: there are many discussions about this situation in this forum. The details vary considerably. As noted, the outcomes vary widely. These discussions often include posts addressing the many factors and circumstances which can influence how things go, ranging from the biggest, most influential factor: how much in breach of the RO the PR is (including how long it has been since the last time the PR was in Canada), to less important factors like personal economic/financial reasons for not coming to Canada sooner. The problem, however, is this forum is populated by a great deal of misinformation in this regard. The influence of factors like personal economic/financial reasons for not coming to Canada sooner being among the more common examples of misinformation. To be clear, YES, the fact that you remained abroad so long because of employment opportunities and related decisions CAN and ACTUALLY MUST BE CONSIDERED in assessing H&C factors IF and when you are subject to a RO examination. Indeed, ANY and ALL reasons why it took you as long as it did can and must be considered.
Obviously it is NOT true that you completely lack H&C reasons. Intent to come and stay and settle is a positive H&C reason. Reasonable explanation of personal difficulty making the move sooner due to employment can be a positive factor but does not carry much weight against a big shortfall in meeting the RO. WHICH leads to Heads-up III . . .
Heads-up III: Even though no one here knows anywhere near enough statistical information to venture a reliable guess about how these situations go at the PoE, there are enough reports from PRs who are reported and issued Departure Orders, both anecdotally here and more illuminating as reported in official IAD and Federal Court published decisions,
to recognize there is a substantial, perhaps high RISK, you will be reported and issued a Departure Order. Thus, that is a contingency you need to be prepared to deal with. Some prospective immigrants are in a better position to make this move despite the RISKS. For many, they cannot handle the financial impact of uprooting the family only to be compelled to leave Canada, be that sooner or, if an appeal is filed and then lost, later.
OVERALL:
Once you are in breach of the RO there is a real risk that upon arrival at a PoE you will be referred to Secondary, subject to questions in Secondary about RO compliance, and then Reported and issued a Departure Order. You and your family will still be allowed to enter Canada. As Canadians (yes, in Canadian law PRs are Canadians) you are entitled to enter Canada (unless and until there is a final adjudication that your PR status is terminated).
Your best chance depends on the first officer who screens you. BUT your best chances also depend on you being upfront and honest (any impression you are being evasive let alone deceptive will dramatically increase the risk of a negative outcome). So you will be informing the officer right up front, just in the customs declaration alone, that you are in breach because you will necessarily need to reveal it has been more than three years since you were last in Canada. Nonetheless, there is a chance this officer will simply waive you into Canada, in which event you are GOOD-to-GO, meaning GOOD to STAY . . . but of course you will then need to stay TWO FULL YEARS to get into compliance, during which time it will be best to NOT leave Canada and NOT apply for a new PR card when your current cards expire.
Otherwise, if referred to Secondary, be prepared to fully explain your situation, the problems you had in making the move sooner, your intentions, and so on, and hope that a sympathetic CBSA immigration officer gives you a chance to come and stay and settle. If reported you can appeal, and stay and work and so on while the appeal is pending, and that too will be considered a positive H&C factor in the appeal. However, generally it is the first officer who is the most lenient, and PoE officers in Secondary tend to be more lenient than IAD panels (who decide the appeal).
BUT . . . TWO BIG CAUTIONS . . .
-- the RISK you will lose PR status (again either sooner or, if you appeal, later) is substantial, a real RISK; so that is something you and your family need to be prepared to handle if you gamble on coming
-- NO ONE here can reliably forecast how this will go for you
OTHERWISE: There are many factors which are likely to influence how things go at the PoE. As already noted, the biggest factor already looms large against you: in breach of the RO by nearly a year, perhaps more than a year by the time you come. In contrast, the sooner you come, the better your chances. For the sake of initial impressions, for example, which can influence how it goes, arriving here before the end of 2019 with a PR card that does not expire until 2021 might be just enough the first officer waives you through. This is not to suggest this is likely. Just to note one among many little details which can nudge an official's decision-making in one direction or the other.
In any event, again there are many, many other discussions about similar situations in older topics here, with a lot of discussion about various factors which can influence how things go. You can peruse those discussions to get a better sense of how various factors MIGHT influence how it goes. That said, it will be impossible to credibly quantify the probabilities. Coming will be a gamble without knowing much about the odds.
