IPod Shuffle 2 no longer updating playlist play count and last played date

I use my shuffle 2 in the gym.  When I'm done working out I sync and the most recently played songs are rotated off using a smart play list.  This is no longer working.  I reset the shuffle 2, I've forced sync and auto filled many times.  My latest workout it still lists all the songs I just listened to in the order I listened to them and has their last played date as many months ago.
This seems to be affecting my other iPod too, but it is tougher to diagnose.  I signed up to iTunes Match and after several days that is still running but I noticed this problem long before iTunes Match became available in Canada.  Both my iPod Shuffle and iTunes are up to date but my music is on an older but upgraded Mac.  It has a G4 so no Lion upgrade, I just checked it is 10.5.8

All my tracks should be MP3s or AAC.  I ripped them myselfs with iTunes.  I may have bought some songs directly off of record labels or some other online music store, but I own my music legally whether I bought it on CD or got given it by magazines or record labels.
I went to the gym today.  I set the shuffle to random.  Some songs were synched back to iTunes but they weren't the songs I listened to, at least not all of them.  Some of them may have been the songs I listened to last workout, at least one or two of the songs updated I did listen to today.
I listened to some other songs last night on my main Mac so it is easy to determine which songs iTunes updated this morning.
I haven't had much time to play with Match.  It is still updating and uploading, it has 6000 songs to go.  That means in a half month of trying it has managed to find and/or upload a little over 1000 songs actually close to 2000 now.  It is something, but it isn't the service I was sold.  All my songs and playlists were supposed to be available in the cloud.  That hasn't happened and in the case of my smart playlists will never happen. 
I'll read you link, but I wrote a blog posting how I was disappointed with the service so far.
Thanks!

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