So anyway, I think you'll be fine with your headset at MAF. I took mine on an airliner trip two summers ago. I checked mine, but I don't see why it would matter.
I have a relatively favorable impression of TSA at MAF. Here's the slightly off-topic story explaining why.
The last time I flew commercially out of MAF, the city police had closed the terminal for about an hour, just as I was arriving. It turned out TSA had successfully done their job, stopping a passenger who had bricks of plastic explosives in his carryon. (The passenger was an off-duty soldier -- he wasn't going to blow up an airplane, but he was very stupid to carry that stuff on a plane). An hour later, after the passenger was taken away by city police, TSA was once again efficiently screening passengers, including me. I thought they did a good job.
On the other hand, I'm much less impressed with TSA at another airport visited by the same guy earlier on his trip. At that TSA location they stopped him briefly when they found he had smoke grenades in his carry on. Upon finding the grenades, they just admonished him (didn't arrest him) and didn't search his bags carefully enough to discover the bricks of plastic explosives that were in the same carryon bag as the grenades. Unbelievably bad job by TSA there.
Anyway, take your headset and enjoy your trip.