Why won't my iTunes let me sync music?

Okay so I'm trying to put some songs on my iPhone 3GS. I made a playlist, selected it in the bit where you check what you want on the device, clicked sync and then checked my phone. Nothing is on here, except existing music.
I thought maybe I had too much stuff so I deleted my old music (un-ticked it all) then synced it again. All music deleted.Re-checked this new playlist. Synced. Still nothing on my device.
Then I thought, maybe it's the playlist? So I individually selected each artist. Synced. NOTHING.
This process lasted well over an hour. I'm not computer savvy, certainly not iTunes savvy, so could someone please help me? I need this music for my Christmas break!

I'm so sorry that I can't answer your question. However you might take comfort in knowing that I'm having the exact same problem: I got my son an iPod Touch for Christmas (gave it to him early for personal reasons) and we can't sync anything!
I'm asking you if I can keep an eye on your question in the hope that it will help me. Hope that is okay with you. Wanted to let you know instead of feeling like a creepy stalker.
Happy Holidays: )

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