Enter-PSsession fails connecting to Windows 8.1 virtual machine

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I’m with Darwin and Olaf on this: step one is configuring PS Remoting on the Win8.1 machine. PS remoting is not a “default on” thing and requires configuration.
Being that it’s definitely not on, I’m confused by this part of your post:

What do you mean by “login-screen”? Like a graphical desktop login screen? Or a terminal based login prompt? PowerShell remoting is an entirely CLI experience so I’m confused by this.