Thanks for Looking at my problem, So to answer all of your questions
1. When you plug it in, does Realtek pop up and ask you what you just plugged in? Yes it does, there is a popup saying that a device has been plugged in and then Realtek Audio Manager pops up with the picture of Headphone box Checked. Then, after hitting OK the box changes to the other picture with the Real speakers out box Checked. SO then I click OK.
2. you're testing it by pressing the "test" option when you right click on the settings dialogue box, right? Plays a little chime and you see the green bars go up but no sound comes out? Yes then after doing the steps above I click Test, see the two speakers illuminate and then turn off and no sound comes through my Bose headset.
3. I might just end up breaking down and buying the USB but I would like to at least get this working for the future, If you could help me out and tell me if you see me doing something wrong that would be awesome.
PS: I saw that you work for the company that makes the mod mic, if I can get this problem fixed with the audio could I use that and the headphones to make this a true PC Headset?