(1). A video card can stream output to both the DVI and the VGA at the same time. By using windows, you can activate both to be on simultaneously. There are a number of different options you can use with dual monitors. (Clone View, horizontal stretch, vertical stretch, etc. )
(2). It might be different for other video cards, but generally, you go to (My Computer/Control Panel/ Display/Settings/Advanced/NameOfYourVideoCard) Then there should be some options on configuring dual monitors. For me, I have an Nvidea card, it won't give me the option to set up dual monitors until I actually have 2 monitors plugged in.
(3). I have never had a mother board with on board video; however, I am sure FunWithFire is correct in that it will automatically disable when you add a new video card. If it doesn't you can probably disable it by going into CMOS before you computer boots into windows and change on board video status to disabled.
(4). I am not an expert on recommending video cards, but I wouldn't think that a jukebox program is going to require to much of the video card. I would try using the video card you have first, and if it wasn't sufficient, then find a new one.
(5). Yes, there should be an option of "Dual View". This should make the primary monitor display the normal section of the monitor, while the second monitor displays extra space, so to speak. I believe that is what you are wanting anyway.
Also, the converter FunWithFire mentioned is exactly what I was talking about. It just changed the DVI connection to VGA.
If I said anything wrong, I am sure someone will correct me.
Just as it is,
Flip Willie