Recently, my my mom has gotten tired of iTunes and is looking for alternatives. Does anyone have any suggestions? It needs to run on Windows, support audiobooks and sync with an iPod. She’s also tech adept (she was a web developer for decades).

Something libre/open would be good, but not strictly necessary.

@kwarrtz Do Winamp or Foobar fit the bill? I'm unsure if they sync with iPods, though.

@Dialectrical I'd looked at Foobar before, and it seems like it might work. WinAmp is intriguing, but unfortunately it doesn't support iPod syncing out of the box and all of the plugins are a decade old.

@tykayn This looks like a really neat idea, but I don't think it's what she's looking for. Running a music server is more work than just managing a local library, and unless I've misunderstood how it works I don't see how it could be used to sync an iPod

I guess ipod are not so easy to make them run something else than what is installed by default. Dunno, never used these apple caged products.
Anyway people can run clients for funkwhale, you don't have to setup a server to use it.
Other paths are possible, like subsonic or stuff like kodi, or ds music for synology. Possibilities are multiple and quite doable for Web dev like me who happens to also be sysadmin on Sundays

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