Simultaneous playback of two sources, with one being Bluetooth, is a rare beast. I suggest checking out the sub for gaming headsets.
If you're down to option 2, then the Audeze Maxwell is an example of a low latency wireless gaming headset that also does Bluetooth multipoint switching. Wireless non-gaming headphones that support "USB DAC mode", i.e. you can use them wired via USB to the PC for low latency, would also satisfy option 2.