Squishypenguin,
My husband just finished improting his car, so I can answer your questions.
In order to get a driver's license, you must get a copy of your driving history from Secretary of State. There is a form that you can find online to request this info. Get it mailed to you. They won't accept a faxed copy and the one that they can give you on the spot at Secretary of State doesn't have all of the information that you need.
Step two, call your U.S. insurance company and any insurance company that you have used in the last seven years and ask for a copy of your insurance history here. Most companies here will not insure you without it and the few that will would only insure you as a new driver and charge you a ridiculous amount of money. You may have to fight with your insurance company to get this, since they aren't very helpful when you are taking your business elsewhere. Hopefully you have better luck with this than my husband did.
Once you have your license and insurance, then you should finish importing the car. Once you import it, you can't drive it with U.S. plates on it, so it is very important to have your Canadian license and insurance first. You can start the process beforehand (US export, Canada Customs paperwork, RIV inspection, safety, e-test) just don't finalize everything with the Ministry of Transportation until you have insurance.