[Crashdummy]

Update: Restarting the displaylink service appears to get the second monitor to run:

|12:44:33|crashdummy@pop-os:[~]> sudo systemctl restart displaylink-driver
|12:44:33|crashdummy@pop-os:[~]> systemctl status displaylink-driver 
● displaylink-driver.service - DisplayLink Driver Service
     Loaded: loaded (/lib/systemd/system/displaylink-driver.service; static)
     Active: active (running) since Sat 2020-11-28 12:44:26 CET; 37s ago
    Process: 19260 ExecStartPre=/bin/sh -c modprobe evdi || (dkms install $(ls -t /usr/src | grep evdi | head -n1  | sed -e "s:-:/:") && modprobe evdi) (code=exited, status=0/SUCCESS)
   Main PID: 19262 (DisplayLinkMana)
      Tasks: 48 (limit: 8913)
     Memory: 73.9M
     CGroup: /system.slice/displaylink-driver.service
             └─19262 /opt/displaylink/DisplayLinkManager

Nov 28 12:44:26 pop-os systemd[1]: Starting DisplayLink Driver Service...
Nov 28 12:44:26 pop-os systemd[1]: Started DisplayLink Driver Service.