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I may be more of a dinosaur than you are thinking. My chief complaints are the switch to the lightning cable which would make all old ipod/iphone accessories obsolete and dropping the ipod classic as a large memory option to have my whole library on one mobile device. That these are not the most robust products compounds the problem. I will have to face that problem of the purchase protected songs from 10 years ago sooner or later.
FYI you can now have ALL of your library on one device even with the smallest iPhone.
The model is changing, it's just that you don't want to. I get that I still have my library and prefer that over having the entire Apple Music subscription.
But I went to iTunes Match for just $24.99 per year they store my entire library in the cloud and guess what it's accessible from up to 10 devices anytime (with internet connection). The entire library. I have 11,000+ songs and could never take more than 2000 or so with me the old way because of storage issues. Now I have it all, all the time, anywhere.
The other option Apple Music is $10 per month and gets you basically everything in Apples library (so 30 million songs) available anytime, anywhere with internet connection. Thats a lot of music.
With both options you can also choose to download music to your device for offline listening like on a plane with only the same storage limitations you had before.
Music takes little bandwidth for downloading so streaming is not much of an issue, it just buffers a little at the start of songs sometimes.
Be sure to backup your library somewhere before using either of these two options because if you delete your music then once you stop the apple service you lose the music too. By backing it up you can always go back later and move your music anywhere.