I have just bought one of the new MacBooks which will cause me to jump a few version of iTunes. I believe that the new separated style wont work for syncing an iPod Classic.
Does anyone have any solutions that dont involve having to keep the old hardware just to sync an iPod. Two versions of iTunes installed simultaneously for example if that is possible?
Best Answer
From what Apple has posted, if you are using Catalina you will no longer be syncing with iTunes, you will be syncing with Finder.
See: https://support.apple.com/en-us/HT201253
It's best to work with actual, solvable problems. In this case, there's nothing to solve. I did a quick Bing search and the very first video Will it Sync? The Original iPod and macOS Catalina provided the information to your question:
Catalina Finder will sync with the 1st Generation Original iPod