Problems with itunes 8 and ipod shuffle gen 2.

Problems with itunes 8 and ipod shuffle gen 2.
I recently upgraded from itunes 7 to itunes 8 on my windows XP PC. That's when i had issues syncing my 2nd gen shuffle.
When i try to drag songs directly on it, itunes says i can't
I made a playlist and use auto fill. But when I remove it from the dock, it's either not updated, or the new songs are at the bottom of the playlist when they are supposed to be up higher. I end up having to hit auto fill twice to make it sync correctly.
Computer Specs
Windows XP SP3
384MB of Ram (works really good)
USB 1.1 connection
Pentium 4 clocked at 1.285 GHZ
IPOD Shuffle Specs
2nd Generation
1GB (964MB)
Version 1.0.4
unchecked options: open itunes when ipod is attached, Sync only checked songs, convert higher bit rate songs to 128kbps AAC, Enable sound check, Limit MAX volume, enable disk use
All those are NOT checked. Sometimes i enable disk use for seeing the IPOD_Control folder, but either way it still messes up.
Itunes Specs:
Version 8.1.1.10

This is a well-known issue. Apple changed the internal file names used with iTunes 8, which makes the ordering on 2nd generation Shuffles behave differently. There is no good workaround, apart from moving the files with a hand-crafted AppleScript program.
Apple has been silent on the issue, so nobody knows if we'll ever have a fix for it or not.

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