Hello,
Apple does state that only 1 external monitor is supported. But it is true, that they could do a better job of announcing it.
Regarding the Startech -it would probably be best if you would contact them directly. But TB3DK2DPPDUE si a Thunderbolt3 docking station - it does not use DisplayLink - so I external monitor should work without any problem (as drivers are already part of macOS).
But USB32DPES2 should be DisplayLink, so if the DisplayLink app is installed and allowed, it should work.
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