What sort of SB player do you have. Are you using mysqueezebox.com or your own local squeezeboxxerver installed on your own computer? Some of what you want is possible with settings adjusted. On a BOOM, you can use the menu to switch between your ipod input and the internet (and by the way, the whole point of the SB players/system is that you can have all your music play through the SB WITHOUT using your ipod). Why use headphone out to stereo when you can use line out? And in any case you can set volume to be variable (adjustable by remote or menu on player). This is one of your player settings. I think there is also a setting about resuming play on power-on, etc. I think you need to fully explore all the menu items and settings. I suspect you can set it up to do what you are asking.
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