when you enter first time to move to Canada, you have to quarantine for 14 days. After that when you travel to US and come back, the officer will ask how frequently will you travel. If you tell that it's once a week, you'll be exempt from quarantine. No need to return on same day.
Also it is not possible to keep US plate and license. When you enter first time, if you tell them that CBSA that are moving to Canada, they will ask you import your car. Once you import, your clock will start ticking for Ontario registration. You need to register within 60 days. For registering you need Ontario license.. so it is not possible to escape from that too. So plan accordingly.
I find Canada to be very strict compared to US in a lot of things and noticed that all their departments work closely. so if you are shifting your residence to Windsor/Canada, do the right way because you'll be getting health cards for your family, you'll get a lease and all that. Skipping license and registration doesn't bode well with settlement.