Windows Media Player vs ITunes

See Getting iTunes & Windows Media Player to play nicely - Apple Community for thoughts on sharing a common library between the two apps. iTunes can make copies of unprotected WMA files in your chosen import format.

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This is not something I have come across for many years but a long time ago iTunes for Windows had the built-in ability to import WMA audio files in to iTunes as long as they were not protected by DRM. (iTunes for Mac has never been able to do this.) I don't know if this is still the case. If not you will first have to convert any WMA files.

iTunes for both Windows and Mac can import MP3 files.

If iTunes for Windows still supports importing WMA files then it should simply be a matter of telling iTunes to import the folder containing the (unprotected) WMA files and any MP3 files.

In terms of the future by far the easiest process is as follows.

1. Always use iTunes to rip any CDs or to do the initial importing and to use preferably AAC or Apple Lossless format but if you prefer MP3 this is also ok.
2. Tell Windows Media Player to 'watch' the iTunes library folder, WMP will then automatically add to its own library music from the iTunes library and it will be able to do this without having to duplicate or move the files. (iTunes cannot be set to watch the WMP library folder this is why it is better to add to iTunes and get WMP to do the watching.)

Since iTunes does not support FLAC, has poor support for WMA and cannot use directly WMA only convert them, and since equally WMP has poor support for AIFF the best formats that both iTunes and WMP can agree on are AAC, ALAC and MP3.

WMP for Windows 10 has full built-in support for AAC and ALAC. It is however possible to also get older versions of Windows and older versions of WMP to also support AAC and ALAC although this will require extra work.

Note: This means it is possible to get WMP to play AAC and ALAC, to support correctly adding to the music section of the WMP library and to even support reading the meta data including any embedded album artwork.

I have my entire music library - all from CDs in Apple Lossless aka ALAC format and shared with WMP.

To add you music to iTunes, click 'File' in the menu bar>then click 'add file to library' or 'add folder to library'. It's as simple as that. Your iTunes library will now include all of your music whether purchased or music you already had on your PC.