It would take a large organization with enough connections to cut through this. You'd probably need to cut a deal so you could distribute their software, and you'd need to provide a mechanism for users to be able to make purchases. Even then, there are various licensing challenges, because you would be distributing the same install, so thousands (or millions) of "installs" would effectively have the same serial or license number.
It's nontrivial, but the basic idea is straightforward and doable. The challenge is how windows software is distributed and licensed, not anything technical.