I cannot help your current problem, but I side-stepped iTunes altogether because I never liked iTunes - for an Apple product, it does not seem all that user-friendly.
I wanted a simple way to directly upload MP3 files to my iPhone and found an app in the iTunes store for a couple bucks that does the trick. It is called “Downloads - Downloader & Download Manager”. It combines a browser, media player and simple file manager. I can plug the iPhone’s USB/Power cable into the USB port on a Windows/Mac/Linux computer and make direct transfers of music, pictures, and video to Downloads folders, using the computer’s own file manager instead of iTunes. WiFi transfers are also possible. I can access and play those media directly within the Downloads program.
I might just try that. I really hate iTunes.
BFL