I never recommend gaming 'headsets', it's always better to get quality headphones based on what you want them for (such as gaming) and slap on a cheap mic imo
I've owned countless headsets in the past, including $150+ options from the Creative's SoundBlaster series. They Never seem to have the sound quality or build quality of a quality set of headphones.
For gaming, typically you want to go for open-back headphones as they allow for more discrimination between lighter sounds such as footsteps. However, because sound also exits out the sides of the headphones, they cause a bit of 'sound pollution' (not a big deal if there aren't people trying to read books next to you haha)
best open-back headphones I would recommend for under $99 is the Audio-Technica ATH-AD700's
I know they're on the edge of your price range, but when it comes to headphones you usually get what you pay for, and considering they usually sell for over $200 you're getting a great deal!
I might be slightly biased since I own the same headphones in a closed-back design, I'm sure there's other good options out there too, but I can't truly recommend something I've never used myself.
Outside of OCN, head over to the Head Fi forums and check out some of the threads over there too. They've got a few super-threads dedicated to rating headphones of different brands and at different price points.
How are you powering your potential headset/headphones? Do you have a sound card or DAC?