ITunes purchase plays in iTunes but not iPod nano

I apologize if this question has been answered and I was unable to find it in a couple of minutes of searching this site and the iTunes help.
I recently bought a 2GB iPod nano. Initially I just used it to listen to MP3s I already had, but recently I bought a song from the iTunes store. I can listen to the song using iTunes / my computer. I can put it in a playlist and sync that playlist with my nano. I can "see" the song on the nano playlist, but when the nano goes to play the song it hesitates for a moment and then goes to the next song.
I have the latest iTunes, the latest iPod software, and I have done a restore to the nano and the nano still won't play the song.
I'm guessing the fix is real obvious, and I simply can't figure it out. Can someone point me in the proper direction?
Thanks!
Dell Latitude Windows XP Pro

If you have made sure that both the iTunes and iPod software are current and have deauthorized and reauthorized your computer, try this test:
1. Deauthorize the computer.
2. Create a new user in the system.
3. Download the free song of the week from the iTMS in the new user account.
4. Play the song in that user account to authorize again.
5. Restore the iPod (using the iPod updater) in the new user account.
6. Sync just the free song of the week and see if it plays on the iPod.
If it does, you appear to have a corrupted iTunes library file, and you should recreate the iTunes library file in your normal user account, and then sync your music back to the iPod and all should be well.
The following articles will help you.
Authorization and Deauthorization.
How to restore the iPod.
How to recreate your iTunes library.
How to create a new user account in Windows.

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Microsoft Windows XP Home Edition Service Pack 3 (Build 2600)
Dell Inc. MM061
iTunes 10.5.2.11
QuickTime not available
FairPlay 1.13.37
Apple Application Support 2.1.6
iPod Updater Library [Error:0000000D]
CD Driver 2.2.0.1
CD Driver DLL 2.1.1.1
Apple Mobile Device 4.0.0.97
Apple Mobile Device Driver 1.57.0.0
Bonjour 3.0.0.10 (333.10)
Gracenote SDK 1.9.5.502
Gracenote MusicID 1.9.5.115
Gracenote Submit 1.9.5.143
Gracenote DSP 1.9.5.45
iTunes Serial Number 0013AB7406B28DC0
Current user is an administrator.
The current local date and time is 2012-01-11 23:19:10.
iTunes is not running in safe mode.
WebKit accelerated compositing is enabled.
HDCP is not supported.
Core Media is not supported. (16005)
Video Display Information
Mobile Intel(R) 945 Express Chipset Family
Mobile Intel(R) 945 Express Chipset Family
**** External Plug-ins Information ****
No external plug-ins installed.
**** Device Connectivity Tests ****
iPodService 10.5.2.11 is currently running.
iTunesHelper is currently not running.
Apple Mobile Device service 3.3.0.0 is currently running.
Universal Serial Bus Controllers:
Intel(R) N10/ICH7 Family USB Universal Host Controller - 27C8. Device is working properly.
Intel(R) N10/ICH7 Family USB Universal Host Controller - 27C9. Device is working properly.
Intel(R) N10/ICH7 Family USB Universal Host Controller - 27CA. Device is working properly.
Intel(R) N10/ICH7 Family USB Universal Host Controller - 27CB. Device is working properly.
Intel(R) N10/ICH7 Family USB2 Enhanced Host Controller - 27CC. Device is working properly.
FireWire (IEEE 1394) Host Controllers:
OHCI Compliant IEEE 1394 Host Controller. Device is working properly.
Most Recent Devices Not Currently Connected:
iPod touch running firmware version 1.1.5
Serial Number: 528239P514P
iPhone 4S running firmware version 5.0.1
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