I moved all my music using the SongShift app on iOS which was super convenient. At least when I bought it, it was a 1 time cost of like $5, not sure about now. But it matches songs and lets you see which ones don’t line up and then copies the playlist over exactly the same.

I had no idea this existed, thanks! My hardware is right at the cutoff for Windows 11 support but still runs strong. I’ll have to play around with this but it should allow me to squeeze a few more years out of it. The windows 10 expiration is definitely making me want to try Linux though.