Car Insurance
#2

When you say 'no record', do you mean you haven't driven in Canada? Anybody can get car insurance (assuming they have a licence of course), there's no requirement to have a minimum amount of experience - you'll just need to be prepared to pay a lot more for it.
#3
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#4
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Aviva worked for both myself and my son the following year when he moved back from the USA. Their website states what is required, and our insurance company in the USA, Geico, was very good in providing a pdf version of the letter stating the number of years with them without making a claim. Aviva also required a copy of my last insurance card in the USA.