Playlists not syncing correctly from iTunes to iPhone4

iTunes is not syncing my playlists consistently. As it is difficult to describe exactly what is going wrong, I'll also list the things that I did to test the issue. I am currently using itunes v10.6.3.25 on Win7 64-bit and iOS v5.1.1 and iTunes Match is not enabled. When I plug my iPhone into my PC to sync, everything appear to go normally, I am not getting any errors. When I look at the contents of my iPhone in iTunes (under the Devices category), it appears to match my iTunes content. However, when I use the Music app on my phone, the playlists/song have not been synced. Here are my attempts to figure out what's going on:
TEST: deleted playlists on iphone
RESULT: playlist deleted on itunes after syncing
TEST: deleted playlists in itunes
RESULT: playlist deleted from iphone
TEST: changed name of playlist in itunes
RESULT: removed *some* songs from playlist on iphone (but not in itunes)
TEST: added songs back to iphone playlist
RESULT: after syncing, songs added were removed from both itunes and iphone playlist
TEST: added songs back to iTunes playlist
RESULT: did not sync songs to iPhone playlist
TEST: added music to iTunes library
RESULT: music successfully synced to iPhone
TEST: added music to a smart playlist
RESULT: smart playlist synced to iPhone successfully
TEST: uninstalled and reinstalled iTunes
RESULT: issue persists
TEST: rebooted iPhone
RESULT: issue persists

I have just started to have trouble playing my playlists on the iPhone. It started to shuffle them and when I turned shuffle off, it would only play one song over and over again. You have to open the iPod and manually advance to the next song. That is obviously unsatifactory. I downloaded the update on the iTunes software today. That did not correct the problem. I also restored the settings on the phone. It wtill will not play a playlist in the order I have it. There is some problem here. I would also be happy to hear a reply on this issue.

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I activated iTunes Match this morning.
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And yes, they relied on other lists...
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IPod Updater Bug Report
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Hi, I apologize about the length of this description, but I believe all or most of it may be relevant.
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