Upgrades apply to the entire Workspace rather than individual boards, so you wouldn't choose a single board to upgrade. Once you upgrade, the bill is automatically calculated taking into account all users in the Workspace.
However, that doesn't mean that all users have to be paid for as part of that bill. That depends on these criteria:
- Members of the Workspace itself are always billable
- Guests of the Workspace are billable if they are members of more than one board. If the guest is only on one board, they're free. So, if those 40 people are only guests on a single board in the Workspace, you wouldn't need to pay for them.
We have some more info on how this works here: https://support.atlassian.com/trello/docs/how-billing-works-with-trello-premium-and-standard/
If you'd like to see in advance how much it would cost to upgrade your Workspace, you can find that by going to the Workspace billing page. To navigate there, click on the down arrow next to "Workspace settings" in the sidebar, and then click on "Upgrade workspace." You'll be able to switch between monthly and annual billing on that page to see how much each option would cost for either Trello Premium or Trello Standard.
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