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no. its a pain and has been a pain for forever. You have to manually go through to do what you are trying and with older products there are always issues.
@JB ive personally had awful experiences with the inreach (messages not sending when I was working leading trips in NH) so I have soured greatly to the idea of ever relying on such devices.
I haven't used itunes/apple music for yeeeears because it was horrible, anti-intuitive and annoying.
Now trying to sort out putting some tunes from my old itunes library onto an ancient ipod for my kids. Am getting nowhere fast. My library has a gazillion tunes in it, but when I plug in the device, i'm only offered about a dozen artists and all of my old voice memos and various other self-generated shit like un-named rough mixes of old band tracks. There seems to be no option for extending what's on offer.
Is there an an easy way of dragging a selection of my full library onto an old device? This seems like it should be pretty basic but I admit to being totally foxed.