@GottaLaff I know you have had expert help. What have been the largest obstacles in your own experience, even with that assistance, and what might you think the obstacles would be for someone of more modest means, trying to do this “on their own”?
@GottaLaff
I went through a very similar experience (almost identical) coming from Canada to the US in 2000. Got my greencard in 2003.
One delay I was my University transcripts were in French (CMR) and getting them translated added a few months to the process.
Back then it was harder but the process of importing your car was tedious. Not so much anymore since almost all US cars have daytime running lights and an speedometer that can switch to metric.
@GottaLaff in case you don't already know. You can be, and many many people, both a Canadian and American Citizen. Canada will welcome you as a citizen if you choose to go through the steps. They do not require you to renounce citizenship. And I know from family that if you are born American, you are always American and can vote unless you go to an Embassy and formally renounce.
All this to say that one day, I hope you become Canadian. You seem nice. ;)