One plex pass account 2 servers

You are logged into your Plex account.
Your cloud server is also signed into your Plex account.
Thus a Plex client knows that the server is yours and lets you access it.

It is possible to sign several servers into your Plex account.
There are no special preparations needed to do that.
You just need to perform the initial claiming strictly according to the book. But there is a potential wrinkle:
If you already have experimented on that computer with Plex server before, I recommend you use this You need to reclaim your server, but don't dare to touch the Windows Registry to sever the link between the old plex server installation and its Plex account (which might not be the same as the one you’re using now).