Unfortunately, no suggestions. Just chiming in to say that you are not alone. I'm having the same issues with playing music on my iPhone 4 since I upgraded to iOS 5. I am also showing a different song on the screen than I am hearing after the first song and, like you, the music just won't play after about three songs.
Hope they get this one fixed soon!
I have a worse problem after the upgrade. The system took over an hours to sync all the music, but when the app is opened, the screens is blank. All it has is the "Store" button on the bottom. When iPod was here, the music played fine, now it seems I have nothing except a 23GB memory hog and no tunes. Anyone have an idea on how to get all them tunes to show up and be playable?
Exact same problem... but I found a solution:
Altered from original solution from Emily P:
Okay, mine now works here is what I did.
- plug in the iPhone, iPad etc
- in iTunes select the phone or iPad
- Under Summary uncheck "Sync with this....."
- Under "Music" uncheck the "Sync Music"
- Let it remove all the songs, dont worry it will come back no problems.
- Once that is all done all the music on the phone or ipad should be gone.
- Now check them both back on, sync, and everything should copy back onto it.
- Working now !!!!!
After letting iTunes update and re-sync with iPad again, then things started behaving. The iOS5 removed iPod and installed a new music player. I think it is the same player with a facelift.
Anyway, once the "glitch" settled down, I haven't had any issues. I think it was a miscommunication between the old iTunes on the iPad and the updated OS. After they were in sync, I was able to update the other apps.