The short answer is yes, it should work perfectly for your setup, but there are a few nuances regarding how the Mac sees the device and how you handle the firmware.
Since your goal is to get better analog control (for driving games) while using the Quadstick as your primary interface, the Wingman XE 2 is actually a recommended tool by the Quadstick community for exactly this purpose.
1. How it works with the MacWhen you plug the Wingman XE 2 into a Mac, the system doesn't see it as a "converter"; it sees it as a standard XInput (Xbox 360) controller.
Because macOS has native support for Xbox controllers, it will be "Plug & Play" for almost any modern Mac game or emulator.
The Quadstick connects to the Wingman XE 2, and the Wingman then sends the signal to the Mac.
You mentioned the difficulty of finding a way to update the firmware without a PC. Good news: Brook recently released a Web-based Firmware Updater.
You no longer need a dedicated Windows .exe file or an emulation solution like Parallels.
As long as you use Google Chrome on your Mac, you can go to the Brook Gaming Support page, select the Wingman XE 2, and use the Web Update button.
This uses "WebUSB" technology to flash the device directly from the browser.
To get that "analog" quality for driving games:
The Profile: You will need a Quadstick profile that maps your sip/puff/joystick movements to the Analog Stickoutputs (specifically the Left or Right Stick axes) rather than just digital "Keyboard" keys (WASD).
The Hardware Chain: Your setup will look like this:
Quadstick Wingman XE 2 Mac USB Port
The Result: The Mac will think a physical Xbox controller is being tilted very precisely. In a driving game, a "soft puff" can translate to a slight turn of the steering wheel, while a "hard puff" gives you a full lock—something keyboard emulation simply can't do.
Compatibility: Fully compatible; Mac sees it as an Xbox 360 controller.
Firmware: Use Chrome on macOS to update via Brook’s website (no PC required anymore).
Analog Support: Works great. Just ensure your Quadstick CSV profile is set to output Gamepad signals (like Left Analog X) instead of Keyboard signals.
Do you already have a specific driving game in mind, or do you need a hand finding a Quadstick profile template for racing?