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The Elder Scrolls IV: Oblivion Hints
Finishing Up
1 of 8: Oreyn asks you to explain things to Vilena Donton, so find her either in the Fighters Guild building or her house.
2 of 8: Tell her about the Blackwood Company and how you and Oreyn worked together, then ask about advancement to be named the new Master of the Fighters Guild. At last!
3 of 8: Then ask her about duties, and she'll recommend that you ask Oreyn to be your second-in-command.
4 of 8: Return to Oreyn and talk to him about advancement to break the news.
5 of 8: After he agrees to be your second-in-command, talk to him about duties to get a key to the special Guildmaster's Chest on the Chorrol guild building's top floor.
6 of 8: What you get in that chest each month depends on what orders you gave Oreyn for that month.
7 of 8: If you told him to focus on recruitment, you'll get more magic items and less gold. If you instead said to focus on getting contracts, you'll get more gold and fewer magic items. (And there's a "balanced" choice of focusing on both equally.)
8 of 8: After a month has passed, you can tell Oreyn to change the focus for the next month if you want to.