If I have one Workspace with 3 boards and have the same 20 users on each board, do I just pay the one time for each user or do I have to pay each time they are added to a board?
Trello Pricing works per workspace, not board, which means when a person is a member of one workspace you pay for them as one member and you can add them to 3 boards as in your case or more with the same price.
In your case, it would be 20 x Standard plan fee regardless of the number of boards even if you add them to more boards. (If your workspace is in a paid plan, and a person is a member of one board only, they count as single-board guests and are not billable).
You pay for:
Workspace members - Anyone who is a member of the Workspace, including admins.
Multi-board guests - Anyone who is not a member of the Workspace, but has access to 2 or more boards in a single Workspace.
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