Thank you for posing the question! The MS docking station has one DisplayPort video output. I think you can use the DisplayPort first, with the 27" monitor. If the 27" monitor doesn’t have a DisplayPort input, you’d need a port adapter or cable (e.g. HDMI-to-DisplayPort). The reason I’d recommend to connect the largest monitor to the DisplayPort is, it’s better to use directly connected video port for high resolution monitor in terms of the performance.
For the remaining two 24" and 20" monitors, you can use Plugable USB graphics adapters. If the monitors have either a DVI or HDMI input, I’d recommend this adapter:
-Plugable USB 3.0 Dual Head Graphics Gigabit Ethernet Adapter (USB3-3900DHE )
This adapter has two graphics ports in a unit, hence it only use one USB 3.0 port of the MS docking station.
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