The main question is probably whether or not FOR YOU it is worth packing up and making the move to Canada
without knowing whether you will be able to keep your PR status. Lots of factors to consider, many of which are personal. In other threads I have also oft noted that even strong H&C cases are tricky. Which leads to the observation by
@canuck78 that (in effect) your risk of a decision terminating your PR status is "
high with 5 years out of Canada." Yep! If you have not been here, in Canada, within the previous five years, you will likely need a remarkably strong, especially compelling H&C case, just to have a decent shot.
And as I have previously noted, remember that if an appeal becomes necessary (whether due to a PR TD application being denied, or a Removal Order being issued attendant the Port-of-Entry examination), the odds of a successful appeal are NOT good.
If you are all in for the gamble, then traveling to Canada via the U.S., as
@canuck78 similarly noted, probably has the best odds of success . . . BUT that is not to say the odds are good. Impossible to quantify the odds any better than that.
Applying for a PR TD may be an advantage if you want to make your best H&C case in the application; this approach could let you know if your H&C case will suffice. If the visa office issues a PR TD you can then travel to Canada knowing you can keep your PR status and safely apply (at least probably; a potentially complicated discussion for another time) for a PR card once settled and working here.
If the PR TD is denied, perhaps reconsider your options.
Note, however, if you appeal a denied PR TD application, again the odds of winning the appeal are NOT good. There is no sign that the individuals who sit for the IAD are more lenient in RO enforcement than overseas visa officers (or CBSA officers acting as the Minister's Delegate), and my sense is the IAD is typically more conservative and strict . . . most of the successful appeals are made by PRs who failed to put forth their H&C case well. This can happen because the IAD conducts a de novo hearing and the PR gets an opportunity to submit more evidence than was presented in the PR TD application, or attendant the hearing with the Minister's Delegate if a 44(1) Report is prepared during the PoE examination.
That is, most successful appeals are for cases which probably had good odds of getting a PR TD based on H&C reasons or not being issued a Removal Order if only the PR had better made their case at that stage. It is not for sure, but it very much appears that for the same facts, the odds are better at the PoE than for a PR TD application, while the odds at the IAD are the lowest.
Meanwhile, even though actually being here in Canada pending an appeal will help a little, it will not make the H&C case very much stronger. It is NOT being here pending the appeal that appears to hurt, handicap the case.
So, if you are prepared to follow through with an appeal, and prepared to come to Canada to stay pending the outcome of the appeal (knowing the odds are not good), as noted above and by
@canuck78, skipping the PR TD application process and traveling to Canada via the U.S. probably improves your odds . . . how much this will improve your odds is impossible to quantify, but generally it appears that PoE officials (CBSA officers) tend to be more lenient in RO enforcement than overseas IRCC officers handling PR TD applications.
. . . "am I correct that I can go ahead and apply for a PR card even if I have an A44(1) written at land border?"
Short answer: yes. Still make the H&C case in that application even though repetitive of what was submitted to PoE officials and what will be submitted in the appeal.
Additional observations: Typically, when a 44(1) Report is written at the border the PR will proceed to immediately be interviewed by an officer acting as the Minister's Delegate (MD), who will review the Report and decide whether to issue a Removal Order, or decide that there are sufficient H&C reasons to allow the PR to keep their PR status despite the RO breach. There are occasions, however, when the MD's review of the Report is delayed, in which event the Report remains outstanding until the MD reviews it (and again, upon reviewing the Report, typically during a telephone or in-person conference with the PR, the MD then decides whether to issue a Removal Order, which the PR can then appeal, OR decides to set aside the Report and allow the PR to keep status for H&C reasons).
If you want to present documents to support your case attendant the PoE examination, including during the interview with the MD (assuming a Report is prepared), be sure to have those IN YOUR HANDS, not in baggage, and carry them in your hands when you go into Secondary at the PoE.
While a person will not be given access or allowed contact with their attorney during a PoE examination, and again this includes the review-interview with the MD, if you have the resources and the means to obtain the assistance of a Canadian lawyer, your lawyer can help you better prepare for the PoE examination, including preparation and organization of supporting documents (note that too many can almost be as much a problem as not enough).
"Due to the nature of my job, a valid PR card is needed for me to travel to US at least twice a year- . . . "
Not sure why you need a valid PR card to travel to the U.S. if you have a passport that will enable you to travel to the U.S.
If you need to fly back to Canada, yes you will need a PR card. But you can otherwise fly to a border destination in the U.S. closest to your destination in Canada and again cross the border by land. If you need to appeal a Removal Order, even if border officials require Secondary screening that should be brief and not problematic for as long as the appeal is pending.