It is a principle of Westminster constitutions that whatever is not prohibited by law is permitted and the common law of the Anglosphere has long held that any ambiguity is resolved in favour of the person who did not set the rules.
Given that, assuming your work permit is for a period of 36 months or less, you qualify. Also, there's no statement on the riv site that hints about the financing state of your car so the fact that you're still making payments on it doesn't affect things. It might matter to your financier, though, so you would probably want to square things with them.
http://www.riv.ca/VehicleAdmissibility.aspx
You only tangentially mention what province. You will quickly learn that matters. :)
Automobile insurance and registration is a provincial matter.
You are not only allowed, you are required to have valid insurance.
https://www.ontario.ca/page/register-and-insure-vehicle-ontario
You also need to get an Ontario driver's licence within 60 days.
https://www.thinkinsure.ca/insurance-help-centre/top-15-ontario-drivers-licence-questions.html
Here is another web page you need to consult:
https://www.ontario.ca/faq/what-do-i-need-register-out-province-vehicle-ontario