I've had the Roost for about a week and a half now, I can choose my milk, beans, and sugar for my coffee, but Brewster won't let me work for him. I go between 11am and 11pm and he always says "Sorry I don't need help right now." Is there something I'm doing wrong? Should I just wait it out and keep asking?
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Oh whoops! Posted this to the wrong spot never mind haha.
If you don't time travel and are currently in October, I think I have the answer. I seem to recall that he doesn't let you work during the first week of October as Jack appears randomly during this time, which counts as an event. It should be available next week.