Hi, I've been having the same problem. I have an iPod classic. I recently used it as a mass storage device to transfer music from my iTunes library on a different computer to the iTunes library on my current computer. When I synced my iPod to my current computer, it did copy every file to it. But once I disconnected the iPod, nothing would appear on it. So I reconnected it, and it still said all the music was on it, even after it went through the syncing process. No music would appear on the actual iPod. I tried the "5 R" solutions, and the step that successfully worked was restoring my iPod. Only then (some 2500 songs later), everything copied to the iPod and appeared on it. But, lo and behold, I reconnected the iPod a few days later to put a couple more songs on and the same glitch occured again. Still, iTunes said the songs were on the iPod, but did not appear on the actual iPod. Photos and contacts still appear. I have the latest version of iTunes installed, as well as the most recent software update for the iPod. I really hope I do not have to restore my iPod every time I want to put a few more songs on it, any help Apple?
P.S. There is one loop hole: When I select certain playlists to be copied instead of the "All Songs and Playlists" option, the songs in those playlists do appear on the iPod, but all other songs vanish; then even iTunes says they aren't on the iPod.