@uveso I figured out a workaround that might only be required because I had another issue I had forgotten about.
I set all my monitors to Landscape and then enabled the NVidia Surround. While everything was in Landscape, I was still able to start the game and then change resolution settings to windowed (game wouldn't accept windowed or resolution launch options for some reason, through steam or FAF or .exe shortcuts). After it was windowed mode, I was able to rotate my display back to profile and the game continued running.
To be extra specific, Windows 10 monitor Display settings still say Landscape and Nvidia Control panel rotation says Portrait. So fooling Windows 10 might be a component of this.