I would strongly advise not letting your nanny drive your kids without insurance. If she were to get in an accident, no coverage would be in place and she would have to foot the bill for damages to all vehicles and potential injuries for your children. Your nanny will need to get insurance for her personal and business use to adequately protect herself and your family. If you have any questions, feel free to ask.
Many insurance policies may cover you in Canada — if it is for short term trips. I would check with your current carrier, but it is likely you'll need to select a Canadian insurance provider if you'll be living there for two years.
Coverage & Claims
Thank you for the question. In short, you will run into issues with your insurance company if you are not listing all household members.
You will both need to be listed on the insurance policy to be eligible drivers. I would put the main policyholder as whoever will be the titleholder and registering the vehicle.
Coverage & Claims
Sorry to hear about the accident. If the other person is at-fault they should cover all damages regardless of who was driving your car.
Car Insurance Costs
If you are going to have historical or classic plates you are going to fall into special types of plans. Personal auto plans that most companies offer will not adequately cover what you need.
I would avoid doing that. You might possibly be able to skirt the laws of NY state by doing this and they may not question you or suspend your license since it would appear you're out of state.
You can still find car insurance without a social security number, but it may be more difficult without a US driver's license. Many insurers will not offer policies for non-licensed drivers.
It's likely that your car insurance company will see if you have car insurance with another company. Most carriers run reports for discount purposes to see if you are already insured.
Unfortunately, I won't be able to tell you about the registration. You will need to contact the DMV for that information.