I ran into a similar issue with my 2018 where it wouldn't play nice without having one monitor feeding from internal. I was trying to feed both monitors through my eGPU and it kept giving me black screens.
Try this and use something like SwitchResX to modify the monitor size or just set it to mirroring.
I use a similar dummy HDMI plug on my headless 2012 Mini Server. Works perfectly without a monitor, keyboard or mouse (which leaves all the USB ports free for external disks) and I can easily access it with screen sharing.
What I am saying is that I cannot enter the logon password because the screen is black because Catalina doesn't fully load. (Anyway that's what I think).
I don't know if this will fix your situation, however I noticed if FileVault is on, I can only log in via a monitor connected to HDMI. Once turned off, I can boot off other video outputs.