Two very good observations.If your current PRC expires in Oct 2020, you are already eligible to apply for its renewal (you can apply up to nine months prior to the expiry date).
This may be beneficial in your situation for two reasons:
. . . . . .
I suggest you discuss the strategy above with your lawyer.
Another thing to point out is that even if your PR card application is approved without your RO compliance being challenged, your shift pattern means that your breach will eventually accumulate to approximately 121 days over a five year rolling period, as you will only be able to spend a third of your time in the country. You may be questioned about this every time you enter and are at risk of a removal order being issued. Whether or not your H&C reasons will be accepted by a CBSA officer is difficult to tell.
The latter warrants emphasis. Even if a new PR card is issued, @toocoolamit could encounter a RO compliance examination whenever he arrives at a Canadian PoE. And compliance will be based on presence in Canada during the five years immediately preceding the date of that arrival. And if the ratio of days present continues to be less than 40%, he will continue to be more in breach every time he returns to Canada.
The regularity of his travel pattern, which appears to include arrivals in Canada approximately every other month and stays for weeks, seems to be one that in itself is not likely to invite RO compliance questions. It tends to suggest a regular and ongoing connection to Canada, suggesting no need to question RO compliance. HOWEVER, there is a significant risk that IRCC flags his GCMS in the course of processing a PR card application, even if it approves the application and issues a new PR card . . . whether that is based on H&C reasons or otherwise.
If flagged, obviously that dramatically elevates the risk that in some future PoE examination he will be referred to Secondary for questioning about RO compliance and, sooner or later, if the travel pattern remains the same (thus always falling a little more short of compliance), quite likely Reported . . . fair chance of not being Reported first or second time, maybe given a warning, but this goes back to a point I made, that CBSA and IRCC are not out to aggressively enforce the RO but that only goes so far, ultimately they have a mandate to enforce the RO and they will.
Even if not flagged, anytime a PR arrives at a PoE and is not in compliance with the RO, there is a RISK of a RO compliance examination and getting Reported. As long as the pattern of travel is resulting in the breach getting bigger, that RISK will increase each succeeding time the PR returns to Canada.
APPLYING FOR NEW PR card SOONER RATHER THAN LATER:
This was a particularly good observation. The first level of inquiry regarding RO compliance is indeed precisely based on whether the PR is in compliance on the date the PR card application is made. For @toocoolamit the easiest measure of this is to count the total number of days outside Canada since the day he landed and became a PR. If that number is less than 1095, he is still in compliance with the RO.
(Reminder: future days within the first five years effectively count as days present in Canada, unless and until the PR is actually absent those days. Thus, for an application made 125 days prior to the fifth year anniversary of the date of landing, the PR is credited with the number of days he has been present PLUS those 125 days, for purposes of assessing compliance when the application is made.)
Obviously far better to make the PR card application while IN compliance with the RO rather than wait to a date when the PR is not in compliance. Even if one readily anticipates there will be a breach of the RO in the near future.
Mapping the potential direction things can go if the PR card application is made soon, while still in compliance, could get a bit complicated. BUT the basics are fairly simple: there is at least a fair chance that IRCC will issue the PR card without any non-routine processing. The PR meets the RO as of the day the application is made (a number of forum participants seem to think this is actually definitive; I am confident that is not correct, but it does illustrate that compliance as of the date the application is made is an important factor).
This could result in @toocoolamit obtaining a new PR card in time to continue on in the same way he has been, that is at least until Reported at a PoE . . . which might happen the first time he returns to Canada once he is in breach of the RO, or it might not happen for months or a year or more, which may depend on whether flagged (due to concerns the PR is "not going to meet their RO" in the future).
Of course there is a risk of non-routine processing, as suggested by @canuck78, but that risk is lower than the risk of non-routine processing if @toocoolamit waits to apply for a new PR card after he has actually breached the RO (indeed, in the latter situation, the risk of non-routine processing is in the range of very likely to almost certain). And that will not otherwise have a negative impact on how things go . . . the question then is whether or not a new PR card is issued before the current card expires, or if he is Reported. Then deciding whether to appeal or not.
By the Way, for clarification: If he waits to apply for a new card after he has already breached the RO (after he has been abroad for more than 1096 days since landing), a referral to a local office for an RO compliance investigation is far more likely than a referral to Secondary Review. This is ordinarily the procedure employed when it appears the PR is in breach of the RO, and then the local office is proceeding to determine whether or not a 44(1) Report should be issued . . . this is the procedure in which ongoing compliance is an issue apart from whether the PR was in compliance the day the application was made.
A referral to Secondary Review is possible, regardless when the PR card application is made. But this tends to be a longer process, during which the PR is indeed flagged, and thus is more likely to encounter the formal PR RO determination the next time the PR arrives at a PoE or when making an application for a PR TD. This is the procedure which could pose the problem of a lengthy period of time between the date the current card expires and a formal decision.
There are also some reports, not many but a few, indicating that sometimes PRs are sent the RQ-related questionnaire directly from CPCPR-Sydney, which can happen months after the application is submitted, which could result in an assessment of the PR's compliance as of the date of the response . . . which if @toocoolamit applies soon for a PR card, while still in compliance with the RO, might not happen to a date after there are more absences leading to being in breach by then. This procedure can then still lead in any of the directions any application is likely to go:
-- approved, PR card issued and either mailed or sent to local office for in-person pick-up, or
-- referred to local office for RO investigation and determination, or
-- referred to Secondary Review