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Month 1: New player update
Month 2: Current player update
Month 3: Old player + Current player update.
Damned if you don't, damned if you do? Well then ask the players what they want first... give them an example of how long things could take, even if "we don't tell players what we are planning, because Supplies"
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A few days after Month 1: threads like this.
A few days during (lol) Month 2: threads like this.