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For number 3, I'll keep you all updated on what the schedule for this will be! I'll give at least a week's notice in advance and schedule a specific time to upgrade so that you all are fully aware of when that will happen.
I'm a little worried about what the upgrade process will be like—I have a feeling I'm going to be using a lot of obscure git commands to get that working. If anyone has any upgrade guides, I'd love to see them! #MastoAdmin