I have an ipod classic 6 generation and a 2016 MacBook Pro (MBP) which I have not updated to Catalina yet. A major reason is 32 bit apps are no longer supported. I am a big audio book listener and Overdrive (the public library book app for downloading audiobooks) refused to update their app to 64 bit! A big advantage of listening to audiobooks on my ipod is the 6th generation is not connected to the internet so once an audiobook is downloaded to my MBP, and transferred to my Ipod, I don't have to worry about library book expiration dates plus it's small and very portable. Now, I have no choice but to upgrade to at least Catalina since my Microsoft Office 2019 suite no longer supports updates. My financial life is on excel so this is the straw that broke the camel's back. I have read about workarounds--i.e., tricking your Mac to think it's Windows, etc. but that is too techy for me. Anyone, know a simple solution to this or if there are any apps out there that would solve it. Wishfull thinking, I guess. My alternative is to listen to audiobooks on my Samsung Galaxy S21. Supposedly Ovedrive is compatible. I would have to deal with the expiration dates. I know I'm whining.....