Transferring iTunes library from Windows 10 PC to macOS Music app

Hello,

I have recently purchased a Macbook Pro and I want to transfer my iTunes Library from my Windows 10 PC to my Macbook Pro. I have a lot of songs which I have spent many hours organising, and I have lots of playlists that I want to transfer to my new Macbook.

I have transferred iTunes Libraries between Windows PCs before by using an external hard drive to copy over the media folder and the iTunes Library.itl file. I then open the .itl file on the new PC and it will open a carbon copy of the library, with the files being readable in the correct location.

However, I am having issues with doing a similar process with my Mac. The iTunes library on my PC has been consolodated and the media folder copied over to my external hard drive. I realise macOS doesn't have a iTunes as such - rather, the Music app - so I copied the contents of my Windows 'Music' folder within iTunes Media to Music\Music\Media on my Mac. I also copied across the .itl file.

I then started iTunes holding the 'option' key and created a new library using the imported .itl file. This successfully copied over my iTunes library so I had the familar layout showing the songs and - crucially - my playlists. However, every single one of these songs has an exclamation mark. I have checked and under preferences the media folder is set correctly, but for whatever reason iTunes cannot find the location of any of my songs.

I then went to File>Import and imported the music files again. This was successful, but it made a duplicate of every file! For each file I had one copy with an exclamation mark (which had data such as number of plays), and another copy that played fine. The songs in my playlists all had exclamation marks.

I know there is a workaround for finding and deleting all songs with exclamation marks, but that would delete the contents of my playlists. For now I've reverted everything on my Macbook to vanilla so the Music app just loads up a blank library. I do of course have plenty of copies/backups of my iTunes library and its content so I've not totally messed everything up.

So, this is what I have tried so far. What is the best way of transferring an iTunes library from Windows to Mac, including playlists? If worst comes to worst I will just import the files into a fresh Music app library and re-build the playlists one by one, though this will take some time.

Just a note as well that evey file I am trying to transfer is an MP3. They come from a variety of sources - CD rip, iTunes, etc - but each file has been converted to an MP3 to make them 'hard' copies. I DJ using iTunes playlists so having the files as actual copies and not just cloud downloads is essential.

Kind regards,

Dominic