Iphone sync issue where recognized in itune, but stops there intermittently

I have been chasing an issue for awhile now. Every now and then, when I plug in my iphone 3gs, it appears to be recognized in the iTunes window, but it stops there and doesn't continue to sync. It acts like I have the preference set to "prevent iphones from automatically syncing" turned on, when I really don't. And again, it only happens once about every 10 times. If I immediately hit the eject button in itunes and plug it right back in, it works and syncs just fine.
I have replaced the phone, the cable, and reset sync history by opening isync app--preferences-reset sync history. Oddly it seems like it happens when it's been a couple of days since I last synced.
The log shows this:
2010-11-07 07:37:06:186|SyncServer|111|6a209f0|Logging|Info| Logging initialized, engine version 578.3 : log level 3
2010-11-07 07:39:06:255|SyncServer|111|6a209f0|Server|Info| Cancelling all sync plans.
2010-11-07 07:39:06:633|SyncServer|111|6a209f0|Server|Info| Goodnight, Gracie.
2010-11-07 07:56:23:444|SyncServer|162|6a209f0|Logging|Info| Logging initialized, engine version 578.3 : log level 3
2010-11-07 07:56:23:748|AddressBookSync|160|6f21a60|Stats|Stats| com.apple.AddressBook: fast sync
you can see the first plug in, then gets "cancelling all sync plans." Immediately pluggin back in, it proceeds as normal.
Any suggestions?

Well, it seems to happen at least once a week. This usually appears in the console log:
11/16/10 7:21:28 AM [0x0-0xf00f].com.apple.iTunes[118] Setting FD_CLOEXEC on all file descriptors
11/16/10 7:21:28 AM [0x0-0xf00f].com.apple.iTunes[118] Initializing child but not closing any file descriptors...
11/16/10 7:21:28 AM [0x0-0xf00f].com.apple.iTunes[118] Initializing child but not cl
11/16/10 7:21:28 AM [0x0-0xf00f].com.apple.iTunes[118] osing any file descriptors...
11/16/10 7:22:06 AM iTunes[118] _NotificationSocketReadCallback (thread 0xa0706500): Unexpected connection closure...
11/16/10 7:22:06 AM iTunes[118] AMDServiceConnectionInvalidate (thread 0xa0706500): shutdown(35) failed: Socket is not connected
If I hit sync button, it proceeds. If I just eject and plug back in it works as expected. I the phone has already been replaced, I reset sync history, changed the cable, etc.
I am still on itunes 921, and plan on updating to 10.1 soon. But if there is anything that can be gained from learning what the issue is before I update, it will be worth it.

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