Credit to u/jabbathenutt_ for being a godsend. Posting their solution for posterity to find.
When trying to connect to a Bluetooth headset that I was already paired with and connecting to, I recently got "That didn't work. Make sure your Bluetooth device is still discoverable, then try again." Attempting to remove the device gave a "Could Not Remove" error.
I reinstalled drivers from my mobo website, restarted countless times, messed with regit, etc. This is what eventually worked for me:
Go to Device Manager and under View make sure to show hidden devices, which will all be grayed out. Underneath "Bluetooth" and "Sound, video, and controllers" devices uninstall every hidden device rega



