A little research shows that the recently-opened 137-km highway from Inuvik to Tuktoyuktuk cost $300,000,000, which leads me to believe that it costs about $100,000,000 per 46 km of highway in Canada's north. Now, I'm not going to pretend that my attempt to use the length the line from Inuvik to Tuktoyuktuk to create a scale and see the length of the yellow lines I'd drawn is anywhere near accurate, but by my quick estimation, the highway system I propose is at least 1,000 times the size of the Inuvik-Tuktoyuktuk span. Not to mention the fact that I have bridges built across the top of Hudson Bay, the Cabot Strait, etc.
I'm guessing that this project might cost at least $500 trillion dollars. That compares to a mere $144 billion for the entire Apollo program. Indeed, apparently the wealth of every person in the world only adds up to $241 trillion.
Still...heck of a road trip.