ogx360 VS BlueRetro

It's a diy design. You can buy premade versions or build your own. https://github.com/Ryzee119/ogx360

Not sure about the brook wingman adapter but the ogx360 does support the 8bitdo Bluetooth adapter according to the GitHub https://github.com/Ryzee119/ogx360

https://github.com/Ryzee119/ogx360 somewhere in the documentation it mentioned a button press combo to invert up and down

I'm not sure it would work unless you were able to split the DC controller port into one Wingman SD, and at that I don't believe the firmware would support multiple controllers om one Wingman. My thinking here is that the DC controller ports are separate and discrete and without a physical connection to each port it would never be able to identify controller 2,3 & 4. I believe we would need something similar to the ogx360 for the OG Xbox to accomplish what your looking for u/mune87

OGX360 which also requires an Xbox 360 wireless receiver

Yes, you can mod the Communicator to use a 3.5m jack. And that seems to work well as long as you don't put high impedance headphones on it. https://imgur.com/a/xisxrwS However yeah, you would have to find a Communicator first... I could see a "translator" being made though, like the ogx360 https://github.com/Ryzee119/ogx360 But instead of converting a controller, it pretends to be a Communicator and interfaces with normal usb and more ideally Bluetooth headsets. Not sure how / if any of that could be done. Just throwing the idea out there. Hard part would be stripping out what you can out of a full HID headset and piping that back into the xboxs simple XID in a way its happy with and still actually works. https://xboxdevwiki.net/Xbox_Input_Devices#Xbox_Communicator

https://github.com/netham45/blueretro - I added a wired controller configuration/mapping to BlueRetro to output commands over I2C in the format that the OGX360 wants.