Help with iTunes playlist sync

Hi,
It seems that newer versions of iTunes (9) do not sync my playlist in the right order. My playlist is a 'smart' playlist and has a ruleset designed to filter for additions to my library that have been recently added within the last couple of months. The problem is that the library order (sorted by 'Date Added' in iTunes) does not sync in said order on my iPod touch 1st or 3rd generation. I am not sure how it is syncing but it's not alphabetical either, it appears to be random as I have looked at all the metadata fields and none sort the playlist how it is showing up on the iPod. If I remember correctly, I had no issues with this with earlier versions of iTunes before 9. So far i've tried, re-installing iTunes and wiping my iPod and resyncing everything which hasn't worked. Just want my playlist to sort the same way on the iPod as it is in iTunes.
Details of the smart playlist i'm working with:
Match All = checked
Date Added - is after - ##/##/####
Genre - does not contain - Podcast
Genre - does not contain - Audiobook
Genre - does not contain - TV Shows
Kind - does not contain - Movie
Grouping - does not contain - book
Kind - does not contain - video
Time - is less than - 30:00
Limit to = unchecked
Match only unchecked items = unchecked
Live updating = checked

Smart playlists are not working correctly in iTunes 9.
Also, your playlist is kinda messed up.
Try this...
Match all;
Playlist is Music
Date added is after ##/##/####
Time - is less than - 30:00 (do you have any songs longer than 30 minutes? If not, delete this)
Live updating enabled
++++
I would not use these...
Genre - does not contain - Podcast
Genre - does not contain - Audiobook
Genre - does not contain - TV Shows
Use *Kind does not contain* instead of *Genre does not contain* because the Genre may not be a podcast or TV Show or Audiobook.

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Smart playlists are not working correctly in iTunes 9.
Also, your playlist is kinda messed up.
Try this...
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Time - is less than - 30:00 (do you have any songs longer than 30 minutes? If not, delete this)
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