Playlist stops after every few songs

I have a playlist that stops playing after playing through four items in the list. I can start it anywhere in the list and sure enough, after playing four selections it stops. Here are some facts about the problem:
- I have all the check-boxes checked.
- Playlist length: 600 entries
- Type: mp3 encoded snippets of Chinese language phrases.
- File size: ranges from 12KB-18KB per mp3 (<= 1 second)
- When it stops the progress bar is about at about 2/3, with the left side showing either 0:00 or 0:01 and the right side showing either -0:00 or -0:01 and the pause button is still showing (as though the selection was still playing)
- It will start playing again if I hit the pause button twice (once to toggle it to pause and then to go back to play)
- All the files play fine individually
- Reducing the playlist size doesn't help
- Moving the files to a new play list doesn't help
- Deleting and re-adding the files doesn't help
The playlist plays all the way through on my iPod without stopping but maybe every 100 entries or so it will play the next 4-8 without any sound and then continue as normal.
I have over 8000 other mp3 language snippets just like these in other playlists but the files are bigger(from 20KB-60KB)and they play through the whole list just fine. If I put files from the offending list into one of the other lists the other list will often stop playing just after that song. I'm curious whether iTunes has a problem handling really small files because this problem was happening in all my playlists of this type until I sorted them into lists of different file sizes. Now only the list with the smallest files (<20KB) has the problem.
Can anyone help?
<br>
Toshiba R10 Tablet PC Windows XP Pro iTunes 7.0.1.8 with 20G iPod

They don't have a clue. I've called a few Apple stores because I have the same problem. Of course no one has heard of this type of problem but is seems fairly common.

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