For #1 and #2, I am not aware of a way that you can use four monitors with distinct output on a dedicated PXI RT controller, and I don't think that USB-VGA adapters are supported.
For #3, RT Hypervisor might be a solution for your application, but there are some caveats. Different I/O resources (like the video output, the USB ports, or the PXIe slots) are dedicated to each of the two OSs, and video is typically routed to the Windows OS. However, the basis for determing what resources can go to which OS gets complicated, so I would encourage you to review some of the existing white papers on RT Hypervisor if you are still interested in this approach. See here, here, or here.
To give you an example, Hypervisor is intended for applications where you wish to do a portion of the I/O on each OS, and I think that at a minimum 25% of your PXIe slots must be assigned to the Windows OS. If all you need Windows for is to provide multi-monitor support, you might want to consider alternatives that keep the real-time processing and display on separate controllers.