Can't Add Music-Please Help

Hi there. Figured I would run down my whole scenario and then hope that you individuals of greater experience and shuffle wisdom could help me. Here goes:
Purchased my first Ipod (2nd Gen 1G Shuffle) a couple of weeks ago. Since then, I have already exchanged it once at Best Buy for a new one. I have never used an Ipod but have used an MP3 player. The computer I am using was previously owned by my brother, who had his own Ipod and Itunes was previously installed on this computer.
Since purchasing the shuffle...:
I can't put any music on the shuffle, using any technique whatsoever. I can't drag and drop, autofill, nada. I have used existing tunes on my computer, tried importing songs from CDs, and even purchased a song from Itunes. None of the songs will go on my shuffle.
In an attempt to fix the problem I have:
1. Restored to no avail.
2. Reset the Ipod.
3. Uninstalled and reinstalled Itunes.
4. Erased all apple related products and reinstalled Itunes.
5. Updated to all the latest versions of Itunes.
6. Attempted to change, tweak, alter all itunes/shuffle settings and reversed those changes, etc.
7. Used apples ipod manuals, answers.yahoo, the whole internet, my own manual that came with my shuffle, and now finally this option (no offense) in order to troubleshoot myself without wasting anybody's time.
I can pretty much say I am at my wits end with this thing. While I'm not an IT or Comp. Science major, I also don't consider myself a complete moron so I'm not quite sure what I am doing wrong. Does it have to do with my bro's Itunes account previously being on this comp? Is it the songs I'm choosing? My roommate has a Nano and she is completely baffled to the point that while she really wants to help, she doesn't want my shuffle touching her comp or her Ipod touching my comp.
Any and all advice is greatly appreciated. Thanks.

Ipod does indeed appear in the Itunes List.
When I drag and drop I get a message at the top either saying "Waiting for IPod" or "Syncing Ipod" for about 30 seconds or so and then nothing happens. The Apple Icon reappears at the top, no song, no message, no nothing.
I have used every USB port on my comp and yes I have used other USB devices before with success.
Thank you for the quick reply btw.

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