Thanks Clint, but in his case, at least as he describes it to me, he ripped a CD using iTunes. All songs from the ripped album play fine inside iTunes on his PC. When he connects his iPad and attempts to sync the album, only *some* of those tunes from that album get copied to the iPad (this issue occurs with many of his albums, not just one). The error message indicates the songs can't be found. Yet, iTunes, which was used to rip the CD, *can* find and play those all the songs from the album just fine.
I don't know what version of iTunes he had on his PC at the time he ripped them (I'm waiting to hear back), but still, there's no DRM and they should be in a file format that is readable by the iPad, no? Sounds like iTunes when syncing is using a different method of locating files than iTunes uses for locating files during playback (again, he had the COPY preference turned OFF when ripping).
I have discussed iTunes Match with him. I, myself, tried the beta when it first came out. I decided to wait for the release. About a month ago, we turned iTunes Match on and have never looked back. My wife and I now have access to some 17,000 tunes across all our devices and computers... well, *some* songs didn't make it to the cloud (which I need to look into) even though EVERYTHING I have in my music library was either bought via iTunes store, ripped in iTunes from my CDs, or imported from Logic or GarageBand. In my friend's case, he has just 3,000 tunes and his iPad has 64GB. He would like to have them physically located on his device until the time comes when he has a library that is taking up too much space - at which point, he'll consider iTunes Match.
Thanks Clint!
- Kevin