Just avoid all Booty Bay quests and it's a lot easier. I started killing the BB members in Faldir's Cove at 39. It's slow going, but you get loot and XP unlike the bruisers later on. I got the "friendly" rep at level 44 (rested most of the time). Sure, you have to avoid the entire cartel, but I did it with an alt anyway :P This seems like a more practical way to do it, if you're doing it alone that is. If you have a group that all want the hat too, might as well wait for bruisers and do it much faster. I'll repost when I get the quest and my hat :)
- Jarobi, 44 Paladin, Earthen Ring
- Jarobi, 44 Paladin, Earthen Ring