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Am stuck at a part where most characters tell me to wait to meet the boss and the other characters are just telling me to complete other quests first, am pretty sure I met the  boss at night and since then nothing has progressed.

There are 2 different tasks:
 - Wait for the Boss to arrive.
 - Meet the Boss.
Both are triggered by sleeping - first in MC bed, next in Rose's bed.

Meet the Boss is a key choice in the game. It sets the storyline to Dark or Good once you get past the meeting.