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I was having a similar problem. I kept getting a "device timed out" or a "disk cannot be found" error when syncing.
However, when I repaired my disk permissions, all problems (and weird iTunes crashes) went away and I was able to sync everything: photos, music, contacts, calendar, etc.
1) To repair disk permissions (on a mac) go to: Applications-->Utilities-->Disk Utility
2) Select your hard drive in the left pane
3) Click "repair disk permissions"
If you get Error 101 after a long wait (this means an actual update is being downloaded) - then to fix it, you need use "Run as Administrator", this is probably because the updater wants to change the contents of an executable file, which is a security risk. So Vista, by default, forbids this action and blocks the program continuing - this shows up as Error 101
When you "Run as Administrator", then the updater is given permission to change the executable so it should work.
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