I had to deal with about the same issue first-hand a few years ago. My daughter's Bat Mitzvah tutor used to give her homework practice on cassette tapes and so I gave my daughter a cassette player to use for it. Even though she knew what a cassette was and what she needed the player for, it did take her a bit of work to figure it out. How to open it was a problem. Then there was the whole A side/B side issue where forward on one side becomes reverse on the other.
My daughter wound up setting things up so that she could use Audacity to create MP3s of the lessons and put them on her iPod.
By the time my next daughter started her tutoring, the teacher had moved to emailing audio files (unfortunately .wma files, but still, a step ahead.)