I have plenty of room on the iPad (latest generation) and all software is up to date. This particular song was purchased through iTunes on PC a couple of days ago. For some reason, even though the song clearly shows up in my iTunes library on PC, and in my new playlist, I cannot get this particular song to sync to the iPad (another song I purchased synched just fine). I've tried wirelessly and with the cable. Each time I try, the "sync" completes with no errors. But then when I check the iPad, the song does not show in the playlist. I actually had just finished successfully synching this song and playlist to my iPhone, so I know it can be done. When synching with my iPad, I've even changed the order of other songs on the playlist to make sure the synching was actually being done, and it is, with no other errors. But this song refuses to show up. Through the iPad itself, I went back into the iTunes store, found the song, clicked on a little iCloud icon next to it, and it finally made it into the "Songs" list on my iPad. But still, no matter what I try, I can't get it to show up in my playlist. Please help.