I think I have figured out the issue with the Insignia Pilot (and probably other MTP/P4S portable players) and Winamp 5.53+ closing without error. The issue has to do with WMP11. When WMP11 is installed it also installs Microsoft User-Mode Driver Framework Feature Pack 1.0.0. This upgrades the MTP drivers, services and other stuff.
Following these instructions from Microsoft (Microsoft WMP11 install/Rollback instructions) to roll back to WMP10, the crashes stopped and Winamp is able to see/connect to the Insignia player once again.
Hopefully anyone having issues with Winamp closing due to MP3 player being plugged in, check for WMP11 and do a roll back.
Following these instructions from Microsoft (Microsoft WMP11 install/Rollback instructions) to roll back to WMP10, the crashes stopped and Winamp is able to see/connect to the Insignia player once again.
Hopefully anyone having issues with Winamp closing due to MP3 player being plugged in, check for WMP11 and do a roll back.
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