As I recall, here's what I didProof of ownership and RIV form are manageable but could US insurance document(need to talk to Geico to check if they provide coverage in Canada) be accepted or the first step is to get Canadian insurance and then followed by registration? Just thinking aloud if this too can be done in the first few weeks or is there any pre-requisite to get insurance too.
1. Called Liberty Mutual and got them to send me a letter that stated my insurance history in the US (7+ years)
2. Called a Canadian insurance company and spoke to their agent. He asked for the insurance history
3. Bought insurance from the Canadian company. They gave me a good rate because my US history was clear
4. Used that proof of Canadian insurance to get the car registered in Canada
5. Once I had the Canadian license plate, I logged onto the Massachusetts RMV and cancelled my US registration
6. Called up Liberty Mutual and cancelled the US policy. They verified that the US plates were cancelled and then cancelled the contract.
The whole process was very simple and straightforward and only took me a day to get it all done.