make sure you are actually signed in when you are syncing up the Zune. check your settings to make sure this is set to happen.
i personally enjoy not having things sync up because sometimes i want to delete something off my computer but keep it on the Zune (e.g. large videos, full seasons of TV shows, Zune specific pictures like the buttons configuration).
as far as not being able to delete stuff until you are in the Zune software...its unfortunately true. you cant delete songs or vids directly from the Zune (hey, MSoft, plz fix this with upcoming updates). you can choose to subscribe/unsubscribe to podcasts directly from the Zune, but thats all i can see as far as changing data.
rock on
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