I found that the most impractical thing with these was that the user interface for selecting songs was typically “you have 200 songs and I’m gonna play them in sequence, if you want a particular song you must skip ahead until you hear it”. It worked for a 12-track audio CD, but felt like an underdeveloped toy feature when used with MP3:s.
I doubt you’ll find any proof that he is against free speech. More like, he cares about other things more than he cares about free speech. Such as his bank account.