I would like to know how exactly you are syncing your device to the MP3 player. I did not have this issue on my 9530 on any of the 5.0 operating systems. I used the audio/headset jack and connected via 3.5mm male to male cable to the aux port on my vehicles radio.
Is this how you are connecting?
I would continue to plug and unplug the 3.5mm jack into your Blackberry device. The original Blackberry Storm has been know to have issues with the headset output jack. Users have been able to initialize the jack by performing the above instruction.
I have the same issue. I updated to 126.96.36.1998 OS and the headset (head phones that came with the Storm) do not work. Tried all this plug-unplug activity without success. Called VZW tech support...no resolution. Downgraded to OS 4.7 and the headset worked just fine. Updated again to 5.0 (because everthing else worked better) and the headset fails to work.
Anybody else have any ideas?