2G Shuffle plays only some of the music loaded on it

As the subject says, when I download songs (either by Autofill or dragging from an iTunes playlist), all the songs appear to be moved to my 2G Shuffle. However, when I try to play them, either in random or straight-through, only about 1 in 4 will actually play. Nevertheless, they continue to appear on the shuffle when I reconnect to iTunes. I have attempted restoring multiple times, and the same thing keeps happening. Also, the selection of songs that it will play is consistent. For instance, here in the summary for one of the songs that will play:
Kind: AAC Audio file
Size: 7 MB
Bit Rate: 256 kpbs
Sample Rate: 44.100 kHz
Date Modified: 12/27/06 12:01 PM
Play Count: 1
Last Played: 1/6/07 4:34 PM
Volume: -10.6 dB
Profile: Low Complexity
Channels: Stereo
Encoded with: iTunes v7.0.2, Quicktime 7.1.3
Here is one that will not:
Kind: AAC audio file
Size: 4.4 MB
Bit Rate: 128 kpbs
Sample Rate: 44.100 kHz
Date Modified: 12/27/06 11:59 AM
Play Count: 0
Last Played: Not available.
Volume: -12.7 dB
Profile: Low Complexity
Channels: Stereo
Encoded with: iTunes v.6.0.4, Quicktime 7.0.4
Has anyone seen this before or have any clue how to fix it? Thank you in advance.

How do you have your Shuffle set up to sync music? 
B-rock

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