How many VGA bypasses (switches) can be used?

I want to use one monitor for my PC, laptop, Xbox, and Dreamcast, all going through the VGA connection. I have a VGA box (Performance VGA adapter) for the Dreamcast that has a VGA bypass, a Vdigi VD-Z3 VGA transcoder for the Xbox, also has a bypass, and plan on getting a 2 port KVM. So, does anyone know how many VGA bypasses can be connected together in a row or in succession / serial? I wonder whether I can have the VGA output of the KVM go to the Dreamcast VGA box adapter (and specifically the bypass), and then have the VGA output of the Dreamcast VGA box go through the Xbox VGA box, and finally from the Xbox to the monitor.