why do I have to pay to use iTunes for music I load from CDs

Your music is in your music library. It can only be accessed on your computer and directly synced to an iPhone. If you wish to access your added music on another device through the cloud or to sync your music libraries across devices, you must subscribe to Apple Music streaming or iTunes Match.

bkdowning wrote:

Thank for the insight. So to be sure, I am paying for a cloud access service. Sort of makes sense. The app itself I just accessing recordings saved in my cloud library then eh?

My understanding is that it is not "pure" iCloud-Drive-style file synchronization.

iTunes Match and Apple Music (streaming service) Sync Library will try to match your songs against ones stored in Apple's database. If they find matches, they may load Apple's versions onto your other devices, instead of storing your files on Apple's servers and copying your files to your other devices.

If you're using Apple Music to do synchronization, and it loads your other devices with files from Apple's database, those files may have DRM that will cause them to stop playing if you ever stop subscribing.

The only other way around this then is to manually download to a stick and put that on my listing device of choice, correct?

I don't believe that iPhones support importing songs directly into their Music libraries from USB flash drives. To load tracks from your own CDs onto them, you use iTunes/Finder synchronization from a library on a Mac or PC.

Correct