I can't drag music from my PC onto my iPod anymore

Just updated to 4.3.5, and iTunes is current also. I had no trouble with it until yesterday, when my iPod temporarily forgot it had any content on it. A PC restart cleared that issue, but now I am unable to put new songs onto the iPod. I drag them from my PC into playlists on iPod, and it greys the track out while displaying the Sync icon (I think) next to the track, but never actually uploads it. The song remains greyed out. Any help is greatly appreciated.

Have you tried restarting or resetting your iPod?
Restart: Press On/Off button until the Slide to Power Off slider appears, select Slide to Power Off and, after the iPad shuts down, then press the On/Off button until the Apple logo appears.
Reset: Press the Home and On/Off buttons at the same time and hold them until the Apple logo appears (about 10 seconds). Ignore the Slide to Power Off slider

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