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Chapter 1: Running the Game / Running Downtime / Longer Periods of Downtime

Average Progress

Source GM Core pg. 47
For long periods of downtime, you might not want to roll for every week, or even every month. Instead, set the level for one task using the lowest level the character can reliably find in the place where they spend their downtime (see Difficulty Classes on page 52 for more on setting task levels). If the character fails this check, you might allow them to try again after a week (or a month, if you're dealing with years of downtime). Don't allow them to roll again if they succeeded but want to try for a critical success, unless they do something in the story of the game that you think makes it reasonable to allow a new roll.

The events you include during a long stretch of downtime should typically feature higher-level tasks than the baseline. For instance, a character Earning Income with Sailing Lore for 4 months might work at a port doing 1st-level tasks most of the time, but have 1 week of 3rd-level tasks to account for busy periods. You'll normally have the player roll once for the time they spent at 1st-level tasks and once for the week of 3rd-level tasks.