If I wanted this functionality, what I'd actually do is just dump every song I've got in one out-of-the-way folder somewhere. Then I'd create the normal folder structure that would have albums in it, but use playlists of the album in place of the actual album. Since you can insert and shuffle playlists into the actively playing one, and these playlist can be made to all reference the same individual file for duplicate songs, you can create the effect you desire, and it could all be done via some clever scripting on the PC side.