I have a similar issue - I have two displays. One is USB-c connection, which I have my Dell D6000 and HDMI monitor plugged into (daisy-chained).
After a reboot my USB-C monitor is not recognised. However, everything plugged into that display including the D6000 works fine. I have to unplug/plug the USB-C monitor to get it working.
So I think the OS issue is with initialising / turning on the 1st external display after a reboot.
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