This question has been asked 1000 times over on other forums, yet none of them have been answered properly. So I'm turning to the great people at TR to shed some light on the subject.
I've got a customer that insists on buying a new iPod (for whatever reason) about once a year. So we always go through the hassle of copying all of his music off of the iPod to his current computer, and then syncing it back to the new device. Well he got tired of using iTunes and wanted something different to do this. I slapped Winamp on his system not knowing what to expect and he loves it... however, the same problem persists. He has well over 8000 songs and only about 6500 of them sync.
I went through his library and found a few albums/songs that I could fix that suddenly allowed them to be sync. For example "Blue Oyster Cult" had an "O" with a dipthong, so the iPod freaked out over the none so standard character. But that only accounted for 31 additional songs and it showed up in the failure to sync menu so it was an easy mistake to catch. I ran a Winamp AutoTag on the entire library hoping it would correct a lot of those issues but it didn't appear to do anything that allowed for more songs to sync. With a library of this size, it just seems stupid to try and manually change everything and check each song for problems. All of these songs seem to play fine in Winamp or iTunes, but I don't even know which ones aren't syncing.
Does anyone know of a good method to check all songs for iPod sync-ability. Perhaps a program that can scan through or notify you if a song has incorrect tags or something along those lines? I'd hate to tell him he is SOL, but I'm also sure they don't want to pay me for many many hours of song by song checks.
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