I'm having a hard time understanding these tweets.
Playing a song and adding songs to 'up next' are two different things. That dialog box has saved me multiple times. What's wrong with it? It only occurs when you are telling iTunes to do conflicting things that it cannot resolve by itself. It's a better outcome than clearing a playlist someone may have spent a lot of time working on.
Software update and login dialogs? Yes those are a thing many apps include. What makes these unique or interesting?
The podcasts menu seems super straight forward to me. Am I missing something here? It says exactly what it does.
Contacting the iPhone update server dialog? Once upon a time Apple's servers would go down under a heavy load of people activating new iOS devices. Presumably the dialog is there to inform you there is a problem contacting the iPhone update servers. Either way I think it's long since been changed.