If I pay American taxes and not Canadian taxes, that's fine. A bit unfortunate because the bracket I'll be in is higher as is the tax rate, but not the end of the world.

The only real obstruction I'm worried about is the legality of doing that work for money. I have some friends who I could employ too, and lots of cash could just sit with the company, but if I can't work for that entity (legally) there's no point in starting it.