I am having a similar issue, except the "sync over wifi" button is checked, but it isn't doing it! It has been days since the last sync and there have been many changes to my devices. Even when I go to try and use the sync button on my iPad, it acts like it is syncing but then stops and doesn't continue. I've rebooted the computer, iTunes, my iPad, etc. and still does the same thing. This is annoying!! The only way it will actually sync is if I plug it in.
