I have 2 computers on which I listen to my music: a Macbook Pro (which I consider to be my "main" computer for my music library) and a Windows 7 desktop, for which the music library was originally populated via iCloud. Both of them are up and running with iCloud and have been for a long time. When I rate a title on one, the rating appears on the other. When I buy a song on iTunes, it downloads to both. Great.
But if I manually add a song to either library, it won't transfer to the other. Instead, the song is visible on the other computer, but is greyed out and never downloads (or even becomes available for download). The songs are remixes from music enthusiasts, so they will never be matched by iTunes Match, but that shouldn't keep them from moving to my other devices, should it?
Does anyone know what is keeping it from transferring, or how I might fix it?