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Bryan, mine does this too. Here's what works for me:
I have it set to sync calendar manually. I've also done my contacts, but I don't do bookmarks as I use firefox.
Open system prefs
Click on the .mac icon
if it opens to the sync tab, it tries to hit the network and almost always gives an error dialog. click "ok", then click on the "account" tab.
It should then tell you "you have xxx days left..." at the bottom. Now click on the sync tab. It'll hit the network, but shouldn't give an error. It should say "last sync..." in the left side of the window. Hit the sync button and it should fly.
This took a lot of fiddling. There were issues between calendars, and at some point I had one calendar I knew was good, then I did a complete overwrite of the central .mac calendar, then synced all other machines after that. Ever since then it has been great...except for this consisten glitch of having to click the account tab, then back to the sync tab. It seems like it doesn't properly close the network connection after a sync, so when it tries to get back on it throws an error.
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