The "what are you trying to plug in" dialog is Ubuntu specific, it's not implemented by PulseAudio itself. If you want your last choice to be remembered, you'll need to talk to the Ubuntu UI people.
Maybe there's something in PulseAudio that could be improved regarding the default behaviour. Can you attach the output of "pactl list" after boot, when you have no audio? Please use the "Add an attachment" link (sometimes people paste long texts to the comment box, which makes following the discussion difficult).
The "what are you trying to plug in" dialog is Ubuntu specific, it's not implemented by PulseAudio itself. If you want your last choice to be remembered, you'll need to talk to the Ubuntu UI people.
Maybe there's something in PulseAudio that could be improved regarding the default behaviour. Can you attach the output of "pactl list" after boot, when you have no audio? Please use the "Add an attachment" link (sometimes people paste long texts to the comment box, which makes following the discussion difficult).