So I'm having a similar issue with my iPod Touch, which I updated to version 9.3 today. The day before, I had transferred an album I bought a few years back onto my iTunes. This was because I had bought the album with a family member onto their iTunes, as I didn't have an Apple account yet. These songs, which I had to manually download because HomeSharing wouldn't work, won't transfer onto my iPod, but they are on my desktop computer's iTunes, and are playable. I've tried manually moving, I've tried re-syncing, but I can't get the album to transfer, along with a song that was released for free online by an artist I follow. They don't appear on my iPod, but when I check the songs on my iPod from my computer, they are all listed there, but grayed out and with the dashed circle next to them.
I was wondering if anyone has been in this same situation, and if so, had they found a solution, and what it was. Please, if anyone has any information, help me out, because this is my single favorite album, and I'm leaving for a vacation before long, and would like to be able to listen on the plane.