Smart Playlists Not Syncing Correct ...

Hi, I apologize about the length of this description, but I believe all or most of it may be relevant.

I have been having trouble synchronizing ANY of my smart playlists. I first noticed it in the playlists I had created which entailed "Most Recently Added" or "Most Recently Played" options. Now I realize that all of my smart playlists are no longer syncing their play order (some too big to determine if songs aren't making it into some of them). For instance, here is the criteria for a playlist I created just to demonstrate this problem (this is a brand new playlist just I made and synced with my iPhone):

Title: Recently Played 5
Criteria: Rating is in the range 3 stars and 5 starts
Checked Boxes-
(X)Limit to [5] items selected by most recently played
(X)Match Only Checked Songs
(X)Live Updating

Playlist as it appears in iTunes:
"Summer, Man" by Taking Back Sunday
"Sink Into Me" by Taking Back Sunday
"New Again" by Taking Back Sunday
"Error: Operator" by Taking Back Sunday
"Swing" by Taking Back Sunday

Playlist as it appears on my iPhone:
"Them Bones" by Alice In Chains
"Hands in the Sky (Big Shot)" by Straylight Run
"Lead Said (And A Paper Anchor)" by Atreyu
... etc

These playlist CLEARLY do not match and it drives me crazy because these types of playlists are what I generally listen to. I'm running iTunes 9.0.1.8 on Windows 7 OS (Dell Inspiron 6400), and OS 3.1.2 on an iPhone 3G. I just recently consolidated my library. I had a collection of over 7000 songs on my external hard drive backed up, and kept about 4000 of them on my computer stored in iTunes (i.e. only the 4000 songs were present in my iTunes library, originating from my laptop hard drive--NOT EXTERNAL). Upon switching to Windows 7, I wanted to have ALL my music on my laptop hard drive and thus copied and re-added all of the music (all 7000). I lost all my track info (ratings, plays, last played date, date added, etc) in this process until I opened the iTunes library file with iTunes(had backed up from before new OS installation) and, voila, all my playlists and track info was restored. I had to do some cleaning up of duplicate files, but nothing major.
I found this thread from Sept. 2008 which seemed to be in regards to the exact same problem under almost the exact same situation: http://discussions.apple.com/thread.jspa?messageID=8066846#8066846. Unfortunately, it's unanswered and archived. My iTunes did not crash, but I cleanly installed a new OS and had to start fresh.

I cannot for the life of me figure this issue out. I thought about restoring my device and syncing it again (which I will try again tomorrow to see if I can manage any progress), but I want to retain my app info and text messages so I plan on restoring from a backup. If anyone has any solutions or even suggestions, I'm open to try anything.

Thanks!

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