I am an avid user of headsets and hands-free kits. And I have widely been opposed to Wireless solutions as they add complexities that just get on my nerves. Batteries, Reception, and Pairing. I have spent way too much time in my life dealing with pairing issues and batteries running out. And when the reception gets a bit skewed, it just gets on me a little bit more.
Instead, I resort to wired solutions for head sets, as well as mice, and anything that I have plugged in and require heavy electric usage. I think Wireless keyboards are one of the few things that I keep wireless. That said, I have been having an issue with too many headsets on my desk. So, as a solution, so that I can simply keep my ear buds in (Very comfortable), I bought a Headset Buddy 3.5mm Smartphone Headset To RJ9 (PH35-RJ9A) to help convert my office phone to work with my phone’s headset.
I’ve considered getting a switch, you could signal Skype from the computer, the Phone, and the Headset all through as sources. I guess this can get to be a bit much and start adding up the wires on the desk, but maybe neatly tucked away, this could be another solution. For now, this should work.