I think this is just a driver bug I have, but I have my headset plugged into the front audio ports on my computer and my speakers plugged into the sound card in the back. They're both playing stereo sound at all times and the microphone is always hooked up. When I want speakers, I turn them on and leave the headphones on the floor. When I want headset, I just turn the speakers off and I'm good to go.
I have a Creative Soundblaster X-Fi XtremeGamer... not sure if that makes a difference but I've found that the front audio ports are an easy way to run my speakers and headset simultaneously.
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