Back to the question of which direction to take first. I would go through the US first. If there's any hiccups crossing the border you will know right away. If you then acquire anything while out west, there's no hassle of then keeping all your receipts as proof of having bought or received items in Canada, crossing into the US and then coming back into Canada. Catch my drift. Your choice, I had some 'splainin to do once, but I had all my receipts as proof. I did the trip from Manitoba back and forth a number of times. I found the leg from SSt Marie to Fargo was okay, west of there, a flatlanders dream. Tie up the steering wheel, lay a brick on the gas pedal and you can pretty much nap all the way. Coffee sucks, doesn't matter which gas/truck stop you hit.