I have to replace my recently broken headset, and wanted to make the best choice. Tell me what you think.
 
Option 1:  

• Logitech headset.

• Logitech microphone.
• Existing earbuds.

The ear-hurting and cheap price are good things to point out. I can say without hesitation that no matter what headset you buy, it will definitely start to hurt your ears over time (no matter how comfortable you think it is!). I'd say microphone as well, but it does tend to pick up more background noise.

I have always hated ear buds, but I guess if your comfortable with them then that might be your best choice.  Did you ever just try to wear the headset less tight?  It doesn't need to be tight to stay on your head.

I have that exact same microphone. It's cheap and good sound quality. I just use speakers.

Use your console headset draped around your neck with the mic in front of your mouth with your earbuds for audio. Just need a stereo splitter Y cable and a micro to mini size converter. Or is that the same headset you were talking about breaking?
 
I went with a bluetooth headset as my PC mic, clipped to my shirt. I recommend a Plantronics brand because of their AudioIQ tech. You can get bluetooth adapter and a headset for the same price as the cheap headset you linked ( http://www.google.com/products?q=audioiq&hl=en&scoring=p).

" I have always hated ear buds, but I guess if your comfortable with them then that might be your best choice.  Did you ever just try to wear the headset less tight?  It doesn't need to be tight to stay on your head. "

" Use your console headset draped around your neck with the mic in front of your mouth with your earbuds for audio. Just need a stereo splitter Y cable and a micro to mini size converter. Or is that the same headset you were talking about breaking?
 
I went with a bluetooth headset as my PC mic, clipped to my shirt. I recommend a Plantronics brand because of their AudioIQ tech. You can get bluetooth adapter and a headset for the same price as the cheap headset you linked ( http://www.google.com/products?q=audioiq&hl=en&scoring=p). "

Headsets are more convenient for me. I'm too lazy to hook up my speakers and both my roommates work nights so it is easier for me. Plus it is just easier to use when playing a game. I talk a lot on steam with friends while playing games though.

logitech headsets are notorious for hurting the fuck out of ears. I suggest either a better class of headset if you can afford it (circumaural with boom mic) or a good table mic mixed with a mid range headset sennheiser (HD550). 
 
Also table mics pick up more unwanted sound on your end when you are broadcasting, versus a headset mic that you can dial in the sensitivity for stuff like voice activated ventrilo speech  
 
ive got the astro A40 XBR headset w/ the mixamp and an auzentech 7.1 soundcard (Dolby digital live setting), good stuff. 

Get a new headset. Honestly, logitech are a terrible brand for headphones. The couple I tried were rotten. Might as well tape 2 tin cans to your ears rapped in nettle. I use Plantronic headphones. Not even a well know brand but are MUCH better than logitech. Super light-weight and comfy.

I personally prefer headset...

I use that desk mic and I absolutely love it. Sounds great + pretty cheap.

The old Logitech Socom headset for the PS2 is great for multipurpose needs.  I used it for the PS2, the PS3, and vent on the PC.  It was a sad day when mine broke after a regrettable occurrence of "rage throwing" it to the floor.