If it's still the client doing the encryption, I'd imagine that with sufficient effort it would theoretically be possible to write an iTunes plugin or kernel module that acts as a proxy, but essentially sits between iTMS and iTunes, saving any downloads as unencrypted files in process. Apple revved the software within less then a week (which shows you where their priorities lay), disabling this fix, and forcing a check that the software connecting is actually a valid version of iTunes. Someone (For some reason DVD Jon's name comes to mind) wrote an iTMS client, that emulated iTunes, bought and downloaded music, but never encrypted it. I don't really follow the iTunes situation, however at one point around 4.6 - 4.7 time it was discovered that Apple actually sends files unencrypted, and they get encrypted locally. But then again, I know nothing of programming or cracking. I find it hard to believe that no one has figured out the trick with iTunes' DRM.
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