Hi @Zed Fernandez - welcome to the Community!
A user's membership status on a board has no effect on billing. If you have upgraded your Workspace, you will only pay for Workspace members/admins and multi-board guests in that Workspace.
If you add someone to one board only in your upgraded Workspace, you won't be billed for them, regardless of if you add them as a member, admin or Observer.
If you add someone to two or more boards in your upgraded Workspace, you will be billed for them. Again, this is regardless of what their membership status is on the boards you added them to - you can add someone to two boards in your upgraded Workspace as an Observer, and they'd still be considered a multi-board guest and billable.
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