Hey there! I work on Stripe Checkout and we recently released an update that should make selling globally a lot easier, removing most of the bullet points in your post.
Ooh, that's nice progress! At TigYog we're actually using Stripe Elements - not Checkout or products - so I think this can't work for us yet. It would be cool if you exposed some of this functionality in Elements. I'm not sure what that would look like though :)