Can someone knowledgeable about this issue comment about legal / tax feasibility of getting a remote job with a US company and living in Canada or elsewhere abroad?
We own shares in the American company and are paid through a Canadian subsidiary. That compensation scheme avoids burdening the employees with the difficulty of declaring foreign earnings come tax time.
So for the most part it's the same as working for a Canadian company, but the pay is better.
I have no idea how it works if your not a citizen. In general i think work visas are fairly easy to get if you are a skilled worker like a software engineer, especially coming from a NAFTA country.