Only if you use the same account on both computers. What means the GP will have to use his work account on his personal computer just to jump into another machine.
Because their colleague wants to let them drive?
Because my sister wants some help installing a program?
There are so many situations where using a computer doesn't involve strict security protocols and heirarchies. Sometimes MS gets a little too caught up in their corporate environments.
And then all your hypotheticals speak to issues which don't involve RDP, at all, which I think shows where this disconnect is. RDP is not about sharing a currently active desktop session between two or more users, so all the hypotheticals you shared aren't the use case for RDP. RDP will transfer that console session to the new RDP connection. So say Alice is signed in to her computer locally, and then wants to ask Bob for some help. She shares the hostname for her computer, and tells Bob their login (a terrible idea regardless of it being a local or Microsoft account). Bob fires up RDP, connects using Alice's account, and now Alice's machine gets disconnected from that desktop session and is sitting at the login screen while Bob now has Alice's desktop session.
This doesn't matter if its a Microsoft account or a local account, this is just how the RDP protocol works on Windows. If you're wanting to have a screen share with the built-in Windows tools, the tool for that was Remote Assistance or Quick Assistant. The usefulness of that tool doesn't change whether using local accounts, domain accounts, or Microsoft accounts. Or just use a different tool altogether, of which there are many.
So, the OP is either having problems using a cloud user RDPing into a domain, or connecting his computer into the work's domain and using the same user all the way.