Itunes no longer imports calendars into my ipod

My first problem was that iTunes would only transfer over certain calendars, not all that I had selected. On top of that, some, but not all, of the start times were an hour later than my iCal calendars. And, I've been having issues with disappearing calendars. So, I restored the iPod and the following happened...
After connecting my ipod to my iMac, I went to iPod options and under calendar, I selected to "synchronize all calendars". iTunes found all my calendars. I clicked ok, iTunes says it's "updating calendars" and after a few moments my ipod is back to normal. But, when I navigate to calendars on the iPod, there are no calendars to be found.
So, I reinstalled itunes. deleted .plist files. I even exported all my calendars to .ics files and completely reinstalled iCal. Restarted the iMac a few times in between. Now, the only way I can get the calendars to show up on my ipod is to mount the ipod as a drive and copy over the .ics files. Since I have 16 calendars, the export and copy routine is not ideal.
I do not sync with entourage. I have a .mac account, but I don't sync with that either. Nor do I have the Mark Space app that seems to appear in a lot of threads about odd times and disappearing calendars.
I have a Gen3 20gb iPod with the latest updates, itunes (6.0.4) ical (2.0.3) and OS X 10.4.6 with 1 GB RAM and about 160 GB of available on the hard disk. My iPod has about 12 Gb of stuff on it.
Any clues as to what's happening or how I can solve this?
imac G5 Mac OS X (10.4.6)

Sorry, it took so long to respond. The computer is connected to the internet via a dedicated DSL line. As I mentioned, up until two weeks ago this was never a problem and really nothing has changed. I tried going under Advanced as you suggested but it came back with "Unable to connect to the CDDB server. The network connection was refused. Make sure you internet connection is active and your network settings are correct, then try again."
Any other suggestions? Thanks

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