Although I do have plenty of "free" software, having a discussion about illegally pirating software is not allowed on these forums, especially when you're motivating him to use pirated software. Guaranteed this thread will be locked soon if it goes on.
If you want to use the music downloading as a comparison, think about this: Did RIAA sue only businesses for downloading music? No, they sued regular people, consumers... If Microsoft finds you, they will indeed sue you, and I'm sure it's happened many of times before.