Leo says to get iTunes Match for a year and replace all his music with 256kb AAC unprotected music. Then, he can do anything he wants with it. Unfortunately, with digital music, he doesn't actually own those files -- he's merely leasing it for his lifetime. They're licensed to him and him only. Since they are unprotected files, though, he could give them to someone else, but they will have his email address in it since they are licensed to him.