As you may have guessed, me and this Brook Wingman are not the best of buddies right now... and at this point i'll copy/paste my long post from over there (sorry if it's too long-winded, I just wanted to establish that I've tried a few things)
Honestly, if there's a magic pill or bullet that I'm somehow missing, please let me know... this thing is causing me some real aggro.
my reddit/dreamcast post:
Okay, first time around (last year some time)
Open package, insert Wingman into Dreamcast port 1, turn on Dreamcast - press button to pair with bluetooth wireless PS3 controller....
Nothing.
Try a few more... nothing. They refuse to see each other.
Attempt to update firmware and fry the unit somehow.
Get another one (today)
Plug into Dreamcast - this time I tried PS3 wireless and PS4 wireless (PS4 is official Sony pad, the PS3 one is a cheap knock-off)
Attempt to pair them and...nothing. They refuse to connect.
Plug in USB cable from Wingman to controllers and the PS3 controller is paired immediately - but the buttons don't work - nothing works. It just appears to be paired.
Try the PS4 and plug in USB - it pairs immediately and the pad works... Great!!
Disconnect USB cable to 'appreciate' the wireless experience - this is why I bought it after all

Nothing, It disconnects immediately.
I have tried plugging in a USB to Wingman to give it a power boost - same results. Nothing.
2nd Wingman, both brand new and sealed.
Can someone please tell me what I'm doing wrong because I'd love to know.
I just tested it on my Saturn and identical results.
Why is this presented as an amazing 'plug and play' solution when the only thing that's right about that statement is 'plug and play'? I have yet to solve my wireless situation. It only works with wired PS4 controller.
In the Saturn, the buttons aren't mapped properly and one of the essential buttons is completely missing. I fired up Burning Rangers and can't get past the tutorial because of this.
Update: I managed to get one controller working - a recently purchased Chinese clone XBOX 360 - using the wireless receiver plugged into the Wingman. I tried a much older, working, 100% official XBOX 360 controller and that did not work at all.
Right now it's back in its packaging and stored away. I bought it because I have all those promised working controllers - but only 1 out of 4 works - and I need that for my PC. I was hoping I could use PS3 or PS4 with it. Well, I can, but only 1 works and it isn't wireless. So it's kind of pointless.