Right, thats the regular process of importing your vehicle, but are you able to keep US insurance/driver license by any means if you're living in Canada? I guess, what if you're not neccessarily living in Canada as a matter of 'residency'. If you're in a border town, you could always visit Canada for ANY reason being a permanent resident (daily). And as long as you're physically in Canada, you're counting the day towards your residency. I don't think CBSA can say NO to your entry daily in Canada no matter your reason for entry.
US health insurance:
I am not sure what you are trying to do but if you move to Canada then its not worth the money to pay in US. Of course you can have US insurance as its you paying the money hence you can very well have coverage in US and Canada doesnt care about it.
But If you are not moving and not a primary residence then there is not question on all of these Canadian related stuff.
US driver license:
Same as above. But you can only keep one license but even if we want to keep both but not seeing much of benefit as both licenses are allowed to drive in non-resident country while being resident of one of these countries hence having both is not required. Not sure why the necessity even if you plan to stay in US as primary home.
Canadian PR residency:
I agree that your partial day counts as full day but it seems that you think of doing it for few times/weeks but you would be questioned on intention to return on same day by doing this for multiple weeks/months.
CBSA can strip you from PR if they can find you having primary residency in US and just visiting Canada for the sake of residency. Having US license and residence in US for months and your short visits will prove that US is your primary home which is enough to report you to the court for terminating PR. PR is for making that country a primary home which should be the intent of PR which is part of the residency definition. Our understanding of obligation is just on the days count which comes after you meet the definition of PR. CBSA guys are not just guards - They are the ones issue you the legal status every time you enter hence they have same level of authority to remove you from Canadian legal status - dont just underestimate while being a foreigner. Just because of being PR, they usually report to the court rather than denying at the border itself - not much difference than any other visa holder.
Even after moving, we are being questioned too many times by both officers for having US plates. And what you are trying is not possible as per my understanding of border commute.
But of course i dont want to discourage you by my understanding hence please give it a try in your way.