IPod Classic updating ratings and not play counts in iTunes

Question

I am currently using an iPod classic purchased in 2010 with iTunes 10.5.3.3.  however I encountered the same issue on 10.6.1 which made me think that if I downgraded that it would solve my problem but it hasn't.
Here is my problem. Over the past two weeks, I noticed that when I synched my  iPod my recenlty played playlist number went from 835 to 720. I typically listen to over  fifty songs throughout the course of the day. I have playlist set up to select songs based on a last played date. Last played not in the last 14 days. I last synched my iPod yesterday and I recently setup a new library that is less than 2 weeks old.
On the iPod everything was working fine. When I synched the iPod I noticed that the playlist reverted back to yesterday's status and that my ratings had changed but not the last played date and play counts did not update. Hence breaking the smart playlist functionality of Top 25 Most Played and any other playlist based on play counts. Also my podcasts are not updating as well. I listened to a podcast today and it is still showing up as new after syncing with iTunes.
I noticed that if I do a hard reset (Menu+center button) and resync then the playlist update from the point of the last. I have not encountered this problem until upgrading to 10.6.1.
I even went has far as deleting the itl files and letting iTunes create them again based off the XML and still the problem persists. I even created a new library and added new songs and the problem persist.
I would like to know a good way to getting the sync functionality to work properly and not just sync my ratings. Has anybody encountered this problem?

Answer 1

The rules for my recently played list is as follows:
Last Played is in the last 2 weeks
Kind does not contain video
Live updating
Oh and I forgot the Match all is checked. 
I have changed my playlist from Apple's default playlist of:
Match all
Last Played is in the last 2 weeks
Media Kind is not Podcast
I have found that Media Kind balloon breaks live updating on iPod Classics but the Kind or Genre balloon does not. In the past I could go two to three weeks without syncing as I have over 100 Gigs of music and sometimes could go into recently played to find a song quicker because it would be at the top. Now that isn't the case.  Most of my smart playlist start with Last Played is not with a certain range so I can listen to new songs and I rate songs as I play them so I can get rid of 1 & 2 star songs off my library at a later date. However when I sync my device the songs reappear  on certain smart playlist with no play counts but updated ratings. Like Mix Rap or 4&5 star unplayed.
For example, Mix: Rap
Match all is checked
Last Played is not in the last 14 days
Last Skipped is not in the last 7 days
Rating is not 1 star
Rating is not 2 star
any
Genre contains Hip-Hop
Genre contains Rap
Limit to 25 items Random
Live updating
I am going by the recently played list because I wiped the entire library as of April 3, 2012 so everything I play is still within the two week window. I have a few other playlist that are not updating after syncing. Meaning they are updating on the device and revert after syncing with iTunes.
After writing my post last night I did a clean install of 10.6.1.7. By clean install I mean I deleted all information from my Users\AppData folder related to Apple Computer in Local, Roaming, and LocalLow. I also deleted my .itl, itdb, and sentinel files and imported my Library xml file. I also performed a super fix on my iPod classic as well.  I played a few songs last night and they seem to be running fine. But that's how it always starts out.
Any feedback would be helpful....Thanks for the response turingtest2 by the way
Message was edited by: dontreallycare4apple