Music app not copying all files from playlist to USB stick

[iGuy73]

I have a playlist with 1000 songs that I want to copy to a USB stick for the truck. In the music app I go to my playlist and select all of the songs. Every time I drag them to the USB stick in Finder it copies only 654 over. After determining some of the missing songs, I've noticed that I can add them to the USB stick one by one. Obviously this would be very tedious - finding the 356 missing songs and dragging each one seperately to add. Does anyone have any idea what causes this?

Edit: It appears that the non-copied songs are from entire albums. For example - there's a 50 song classic rock compliation, these files won't be copied when I select all 1000 songs from the playlist. If I only select these 100 songs (or any amount of songs from this sampler - or any other affected album), they will be copied over.

Edit 2: I just imported the playlist into the music app on our MacMini which has pretty much the same library/music (a few songs couldn't be found but they're not completely synced). In the music app on there I selected all 1000 songs (minus the few missing that couldn't be found) in the playlist and dragged them to a USB stick and everything copied over just fine, all songs that the MacBook will not copy were copied on the MacMini.

(instead of USB stick I've also tried adding them to a folder directly on my desktop - same issue there)