The first version of iTunes on OS9 probably does support Apple Events over localtalk, and so it might conceivably work.... Sounds to me like an ideal Retro Challenge project.

The floppy probably just needs cleaned and lubricated. In my experience, the grease on the motor gears etc. is often pretty hard by this stage, but like everything mechanical, it can be renewed. The challenge of doing that/ learning to do that is part of the package.

Check out this site for a treasure trove of Compact-era applications.