I once read a composer complaining that iTunes has deleted his master records and "helpfully" replaced them with compressed files (lossy compression of course). I tried to find it to prove your point, but found this instead:

https://discussions.apple.com/thread/250315803

Software that loses data it fetched or produced is an accident. Software that actively search for and deletes data it has nothing to do with (in backups!!), is malware. People went to jail over such things.

There are many iTunes stories like that. A friend of mine who is a composer and singer had his original songs erased from his library, irreplaceable live recordings, because of Apple's open hostility toward files they didn't create.

iTunes was SoundJam MP with an Apple makeover. Both SoundJam MP and Audion were the shit at the time, so I recall being thrilled at the acqui-hire.

Why specifically do you hold iTunes in such low regard? The bolt-on, beyond-music functionality has always sucked, but I didn't find it wanting from a music management POV. (Although I never used it for ripping. dBpoweramp for me, thank you.)

iTunes was never as good as any of the free music managers out there at the time. It lacked most serious features that users with a real collection (of their own) might need. Anything related to finding, sorting, organizing, naming, changing metadata, moving, sharing, re-ripping, ripping at all, etc. were severely crippled. Perhaps that's because SoundJam didn't build those features. But they stayed unbuilt because Apple didn't want them.

As far as the raw UI, they were shown to the door by Zune which was a massive failure! Couldn't Apple with its money and music business success have made Zune or something even better? Of course they could. They had an early lead. My point is they chose not to because openness and control in music (or anything else) is antithetical to their business model. This adversarial view of users is also what lead to terrible iTunes bugs like eating your music, which others also recall well.