Prerequisites: Max out Osman's level 2 friendship
Reward: None
Unlocks: Osman level 3 friendship
Moonbury's chief of police isn't the friendliest guy, especially to newcomers, but helping him out certainly warms Osman to your presence a little. If you want to bolster your relationship with him even more you'll need to continue the practice of hunting him down around Moonbury. Osman doesn't stay in any one place for long, though if you want a predictable spot to locate him you'll most often find Osman behind his desk at the Police Department.
Once you've maxed out the second level of friendship with Osman he will post a note on the Bulletin Boards of Moonbury, ordering Derrek and Dean to attend a meeting at the Police Department or face a fine. You can watch the brothers get chewed out between 8:00 and 22:00, any day of the week. (In other words, you can go there at virtually any time to see the cut scene.)
The meeting goes poorly, and Osman yells and the brothers for not filling out a report that they most definitely did. Things get worse as Cassandra, Osman's wife, comes in, and the police chief leaves in a huff. Everyone decides that Osman needs a day off, and Derrek asks you to make an official request to Mayor Myer. You'll typically find Myer at Town Hall, during operating hours, behind his desk on the second floor.
Myer is all too happy to give Osman a day off, and sends you out to find the poor, overworked fellow. Look for Osman in Moonbury and the both of you will jump right to Myer's office to discuss the situation. Osman will agree that he's been working too hard, and take a break. The quest will end, and you'll unlock the third level of friendship with Osman.