Personally have not pre-ordered the PS4 Pro. The features do look pretty nice, but I'm saving money currently and have opted to pass on the PS4 Pro.
As for a headset, I will throw a vote in for Turtle Beach. Got a pair of PX22s last year and love them. No issues with them at all, use it for my XB1/PS4/PC needs.
Able to wear the headset for prolonged periods of time with no discomfort. Feedback feature is amazing, and there's a slider to adjust the severity of the feedback.
You also get a bass slider, treble slider, chat volume slider, and game volume slider. Multiple ports for various setups.
I have a setup that is universal for PS4/XB1 so I don't need to use different cables when I switch consoles.