With the 22nd anniversary of the iPod having occurred on October 23rd, which was your first iPod?
Here’s a picture of mine. I have it, along with several other previous models.
this post was submitted on 24 Oct 2023
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No FLAC, but ALAC works on iPods.
As for iTunes/Music; I kinda like it. It's fairly straightforward since they stripped out all the other stuff.