So overseer will reward you with McKenzie's Special Brews, but when I go to spend that brew with the old man, he has nothing available. What's up with this? Is there faction required or do I have to actually do a mission before he will sell me something? I would hate to think that I wasted time on this when I could have just gotten some added exp or something.
Each group mission unlocks specific loot from that mission + some others. Each raid unlocks specific loot from that raid + some others.
Yes, you have to unlock his wares by doing missions/raids. 1 win of each mission/raid, should be enough to unlock everything he has.