"Smarts", in my experience, is also a widely relative term.
I'm using #icecast and #darkice. It was very simple to set up. Well, not taking into account my #alsa / #JackAudio configuration, which wasn't simple to set up, actually.
As an aside, what sort of #Bose headphones do you have? I have a the crazy expensive sound cancelling ear-bud types that I use, though I prefer my #Bayerdynamic over the ears for mixing / serious listening at my computer.
#icecast #darkice #alsa #jackaudio #bose #Bayerdynamic