What is the chances of entering Canada after me and my family's PR cards are expired since 5 years ago and my RO was not met?
I am outside Canada for two basic reasons,
1. My mother is quite old 68 years and she made three spine surgeries and she likes me staying
2. I am currently in a good job that I could not find a replacement to it in Canada.
I do not disagree with other observations emphasizing the odds are NOT good that you will be allowed to retain your PR status. The length of the absence looms rather large.
While it appears your chances are NOT good, I strongly disagree with declarative assertions as to what the result will be. NO ONE here can fully assess and determine with certainty what the outcome will be in an individual case. Even if they are apprised of far more information about the particular case than is presented in your query.
And it is simply
NOT true that financial or employment reasons for remaining abroad are NOT considered as potential reasons for justifying the retention of PR status notwithstanding a breach of the PR Residency Obligation. How such factors are considered can vary considerably. Indeed,
ANY and ALL reasons why a PR remained abroad MUST be considered before an officer can make a decision resulting in the denial of a PR Travel Document application or the issuance of a Departure Order attendant a 44(1) Report for Inadmissibility.
Which should NOT be understood to offer much hope. And the longer you have been outside the Canada, the lower the odds of getting, in effect, a waiver for the breach the RO.
Some procedural observations:
If I can enter Canada, will it be better through applying for a PR Travel Document (from a Canadian Embassy) and then air travel to Canada, or would it be better to directly go through the USA border using my expired PR card?
Is there a chance that the Canadian Embassy not issue the PRTD and instead of that report me?
Generally, so far as we can discern, in PR RO related decision-making border officers at a PoE tend to be more lenient if not generous than Visa Offices. BUT your circumstances appear likely to evoke a negative decision
either way, UNLESS your situation, as best you can describe and document it, convinces the respective officer that you should be allowed to keep PR status based on H&C reasons.
Whether your chances at the border (traveling via the U.S.) are enough better, compared to making a PR Travel Document application, to actually pack up and make that move, leaving employment where you are now, settling affairs, and so on, is a tough call. Again, your odds do not appear to be anywhere near good. Either way. Thing is, if you take that gamble, best case scenario is you are allowed into Canada without being Reported, and if that happens that will only work if you STAY in Canada for the next two years. Of course even if Reported and issued a Departure Order, this way you can still enter Canada and stay and appeal, and by staying until the appeal is heard thereby improve the H&C case at least some. But the odds still do not appear favourable. Rather the contrary.
So whether it is worth doing that is very much your personal decision, versus just putting it all into an application for a PR TD, explaining and documenting, as best you can, your reasons for remaining abroad so long and explaining your desire and intent to now make the move to Canada to stay, and letting the Visa Office decide based on what you submit.
Odds are not good. But, again, NO ONE here can reliably say for sure how it will go. And if the Visa Office views your reasons, your explanation, justifies giving you the chance to come to Canada and keep your PR, a favourable H&C decision and issuance of a PR TD would mean you could come to Canada confident you will be allowed to stay, keeping PR status.
For now you are still a Canadian. Albeit a Canadian who has not met the obligations for keeping Canadian status. You are largely at the mercy of the officers who will examine your case and determine if your reasons for not meeting the obligations for keeping Canadian status justify giving you the chance to keep your PR status. Up to you whether you want to make the move and hope it goes well at the border, or whether you let it all hang out in a PR TD application hoping the Visa Office gives you a break.