At one point (couple times actually) I had my pilot in game fling his gaze to the bottom left each time I went into cockpit (which makes me think it was finally connecting but giving bad values)
Well, at least it seems like ISE has written the correct settings to the binds-file. When the view is at the bottom left then that means that vjoy has both it’s axis set to zero which in turn usually indicates a “broken” vJoy (most likely compatibility issues with another HID).
Do you get any error messages if you start “Joy Configuration” or “vJoy Feeder”? (Make sure to quit ISE first)