iTunes Match: $24.99/Year, Matches Ripped Tunes, Offers Them In The Cloud: As far as ripped music, iTunes has 18 million songs in the music store and Apple will use a feature called iTunes Match to give users the same benefits on ripped songs matched to iTunes songs, as with purchased tracks. A user's library is scanned and matched and any songs that remain unmatched can be uploaded for syncing. Songs that are matched are upgraded to 256KBps, AAC, DRM-free, with all the benefits above, including push syncing and all the rest.
iTunes Match is priced at a flat rate of $24.99 per year, even for "20,000 songs."