Im in the same boat sort off. I love my ipod classic 160gb. Still works fine, i stil rip cds to it. my question is the future. I never got at ipod touch only because when they were producing them up till near 2018 the highest capacity was 120gb at best till they finally increased to 160gb at $399 price. im planning to get a new mac this year making the jump from intel to apple silicon based macs, so if i can buy a ipod touch with whichever new mac i buy, will it work with the new macs? Also would my ipod classic still work with a new mac? What other higher capacity mp3 players out there work with itunes/\macs in 2023??