Sorry, have to go to bed.
1) Google Manycam, go to Justin.tv, and set up your stream from there. Simple.
2) I stream video games, like Persona 4, Tales of the Abyss, Fire Emblem, and Halo/other FPS games. I think that would be considered entertaining, no? I do that "boring" spriting thing as well, which, I admit, is normally more fun for the person who is doing the spriting rather than for the person who is watching.