Sync iPod Nano: receives only outdated Contacts

I recently bought an iPod Nano (4th generation? early August 2006). I have tried to synchronize my contacts and calendar with it, but in both cases the iPod displays outdated information: an old version of my calendar and an old version of my contacts.
I have had endless problems synchronizing with my .Mac account, too, which no one has been able to solve.

Some more information: I just restored downloaded iTunes 7 and restored my iPod to factory settings. I updated my addressbook manually.
Then I synced, using iTunes 7.
An address book was copied, but it is a completely out-of-date version of my address book. What gives?

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    This is perfectly normal, some of the listed capacity is used for formatting and other functions including the iPod's operating software. You'll see the same thing if you connect any flash memory stick. For instance my 8GB USB memory stick is reported as 7.45 GB. The same thing happens with hard drives. With hard drives, there's a difference between how manufacturers calculate capacity and how the operating system calculates it. You'll see an example of that if you look at the size reported for your own computer hard drive. My 300 GB hard drive is reported as 279.36 for instance.: How much content will fit on my iPod?

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