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Jan 6, 2016 9:28 AM in response to THEMagicMissileby brenden dv,Hi THEMagicMissile,
Welcome to the Apple Support Communities! I'm sorry to hear you are having these intermittent but persistent playback issues with iTunes. From your description, it sounds like iTunes may be hanging during playback (especially the part about needing to force it to close from the Task Manager before relaunching window). If that is the case, you may find the troubleshooting steps outlined in the following article helpful:
Fix unexpected quits or launch issues in iTunes for Windows - Apple Support
Regards
