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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.
 
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.
 
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