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This will happen if WiFi isn't connected. After resetting, are you able to get it to connect to your WiFi network?
That's actually a great idea. Is that how you normally sync? If so, it should work - it should also do the update that way if there is one avalable. You can force the sync using the sync icon on the desktop. IF you have any question about doing that let me know.
You can also do a complete reset of the device if you can get into the menu. If all else fails, this should correct the problem.