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I hooked up an external CD drive to my Mac Mini and I've been loading in my CD collection.
For example, Billy Joel's "Greatest Hits" album, which is a 2 volume set. On the iTunes store, it's listed as a single CD. So iTunes cannot find the freaking albums if you load them in as two CDs. ***?
I manually added cover artwork to both. But Match only downloaded Vol 2 onto my iPod Touch. It loaded both albums to my MacBook but not the artwork for Vol 1.
When I connect the iPod to my MacBook or Mac Mini, it's impossible to download Vol 1 of this album onto the iPod. In fact, iTunes thinks Vol 1 *IS* on the iPod, when it's actually Vol 2 that's on the iPod.
When there are obvious errors between iTunes and my iPod, I can find no way of fixing them. I can't delete the albums through iTunes because it's already confused about what's on the iPod. I can't do anything on the iPod side. And Match is oblivious to the errors.
I have reset my iPod twice now, removing all content and reinitializing it. Match pushes down whatever it thinks is there, errors and all, and there's no way to make any corrections that I can find.
I've also got lots of albums that are not available on iTunes. I can't find any explanation of what Match does when this happens; all I've found is descriptions saying that when you load your albums with Match activated, it will download the songs to all of your other machines in 256-bit AAC encoding. If an album isn't on Match, iTunes cannot find the artwork, and often Match won't download the artwork either, because I'm guessing it's looking for it on iTunes. The artwork shows up in iTunes, but it can't be forced down to the iPod. So I get a big grey question mark. You can lookup an album in the iTunes store, but you can't tell iTunes "this is the album I've got". If there's not an exact match in some of the metadata, you can't get them to sync up.
Many songs I have uploaded as parts of entire albums on my Mac Mini won't download onto either my iPod or my MacBook. I get a generic (and useless) warning saying "iTunes cannot download the song you've selected". Nonetheless, these songs ARE on my Mac Mini, the CAN be played, and there's no way I can find to tell iTunes to RE-UPLOAD them. In most cases, these songs tend to be the first song on the album.
I don't understand what is so complicated about all of this that the metadata for the albums has to be so tightly controlled and that there's no way of pushing updates to metadata down to the iPod, or even correcting it on the iPod directly. I'd guess that iTunes uses the metadata to sync everything. But when there's a discrepancy between a physical album and what's on iTunes Store, there's nothing that can be done about it on the customer's end because it seems that "iTunes Store Rules"