I’m not sure. I was testing out my old iPod so I only put 10 songs on just to see if it worked with the fresh battery and SD card storage I installed. Apparently I cooked the motherboard in such a way that the audio doesn’t work. It’s a somewhat common problem according to the internet.

I’ve got my own server but I wanted to give this a try for fun anyway. iTunes seems to have no problem using a library that lives on a local server and syncing it to an iPod. I’m guessing you need a windows computer or mac to run iTunes though, it’s been over a decade since I last tried to get it to work on a Linux machine

But it all lives in a big cheese grater