> Replicating the experience of using something like Smalltalk transcript window.

As far as I know from Pharo, the Smalltalk transcript logs plain text and is less capable than xterm. So what you care about is not the capabilities of the terminal but having a long-lived interactive session/REPL or a REPL integrated with an editor?

> No need for SSH to talk with Windows Core/Nano, it can be done via Web GUI administration, or PowerShell remoting.

I was thinking of the administrator connecting to Windows from their Mac or Linux/BSD machine. I don't know if that's a good idea compared to them getting a Windows VM and using Windows-to-Windows PowerShell remoting as you suggest.