Run the Windows Media Player troubleshooter and check if it helps. I appreciate your efforts taken to resolve the issue and would suggest you to try the following methods to diagnose issues with Windows Media Player (WMP) and check if they are helpful.
In order to provide you with better assistance. However, I would appreciate if you could answer a few questions to narrow down the issue I can imagine the inconvenience you are experiencing while creating playlist in Windows Media Player and will certainly help you in the right direction to fix the issue. Thank you for posting your query in Microsoft Community.