Delivery is currently scheduled for DisplayLink Manager release 1.6 for the end of November for Apple M1 silicon running macOS 12 Monterey.
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After 2 hours of troubleshooting, I finally was able to get rotation working on Catalina 10.15.5. My setup is 3 externals, 1 ultrawide as main and 2 smaller screens left and right. I have my left screen in portrait orientation.
1) Install Legacy driver 5.2.5 https://www.displaylink.com/downloads/file?id=1636
3) For me, I had to unplug and replug power of dock to get Dell D6000 dock to recognize all 3 externals
4) If for some reason System preferences is already open, CLOSE IT
5) Move your mouse to the screen that you want to rotate
6) On -that- screen, Apple Icon -> System preferences
7) Hold down Option + CMD keys and click 'Displays' in the System preferences
8) You should then see the 'Rotate' option -only- on the dialog on the screen that actually opened 'Displays' from System Preferences.
TLDR: The rotate option only seems to show on the screen that is actually opening system preferences -> Displays.
Really painful to figure this out but it works for me.