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I used to have iTunes to put music on my iPod but I found it very bulky and Apple is a PITA to control on the PC. I switched to PodoX for that purpose.
I've used iEatBrainz for this and found it required a lot of manual intervention to make it work. iEatBrainz would come up with as many as 10 possibilities for the song associated with a music file and the user has to manually pick the best choice from that list. Easier than manually typing in the info, but still quite a bit of work if you have a large iTunes library. How much better does this work?
I really hate iTunes, Winamp isn't bad but I like Foobar2000
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