Thanks for the suggestion. I was going to try today and plugged in my USB today for one last try. WMP recognized and sync'd the music. I have no idea why it started working again.
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Perhaps rebuilding the Windows Media Player database might resolve the issue.
Here's a link wherein similar issue is fixed by clearing the corrupt database:
Please refer to the suggestions that are marked as answer.
You may even try restarting/turning ON the "Portable Device Enumerator Service":
Let us know the results.
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