With iTunes match, do you actually get the replacement song files downloaded to your computer, or do you just get the matches "in the cloud?"
In other words, could I subscribe to iTunes match for one year and get all of my ripped songs from iTunes and then drop it a year later and continue to have my songs matched in the cloud since I now have "official" iTunes files on my computer?
I *believe* that Apple is going to give you the actual file to store locally. However, whereas a normal iTunes purchase would be available via iCloud sync to all devices, the iTunes-matched music that you never actually purchased through iTunes would only be available if you have your current $25 per year subscription. Apple does have a record of every song you actually purchased from them through iTunes.
So the scenario would go like this....
1) Rip 100 CDs
2) Get iTunes Match and get iTunes digital files for everything ripped
3) Use iCloud to effortlessly move music between your devices whether bought on iTunes or matched by iTunes
4) iTunes Match subscription expires
5) All your iTunes Match music that has not been purchased can no longer be synced over iCloud, but you still have all the digital files so that you can sync them manually
Your alternative is to buy the music directly on iTunes to avoid the recurring fees. Basically, Apple is selling you the synching service and giving the music industry a cut. The music industry likes it because it creates a recurring revenue model for them on music they previously got nothing for, and if you don't like the recurring revenue, but like the iCloud service then maybe you will repurchase (or first-time purchase) the music that you ripped.
I imagine many folks actually purchased CDs as opposed to downloading bootlegged copies. But iTunes Match will treat those the same way.