In this case, I would suggest utilizing the Unattended Access feature, I presume when you plug off the monitor something happens that prevents the system from sending the signal correctly and you won't need to plug in the monitor at all. Here is the guide on how to do this:
Just tested it with my colleagues and Powerpoint and everything worked perfectly, we have disabled - Always On Top mode by pressing a small gray pin in the connection panel, after that opened the presentation and it have never appeared during 40+ slides clicked through. have you tried doing it that way?
That is correct, I can see the encryption key, and on the host does the Use Encryption option is enabled? It shouldn't request PIN in case of encryption enabled it should not request the PIN and ask for the encryption key instead.
That is correct, the key should be the same on the host as on both connecting clients. So if I understood the question correctly - yes, you can use the same key.
As an addition to my colleague's commentary, we are releasing a feature in the upcoming version which will allow your junior to observe the work of the senior. just wait for the version 2.2 to be released.
Quick Support is a light version of CloudBerry Remote Assistant that allows you to join a remote session without product installation and administrator permissions on a workstation. This is why I recommend using the full version.
In this case, you described everything correctly, the workaround so far is to use remote upload of files. You can click the same button on the remote machine and upload any files you need to your machine. We surely understand that this is not perfect and already designing it anew. I have added your request to an already existing one, you will be notified upon release.