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G.N.E.R.D. Rage
I've heard more complaints about G.N.E.R.D. Rage than any other Hallow's End achievement. It mostly revolves around whether you're comfortable hanging out in the battlegrounds for long periods of time. Essentially, one of the types of candies you'll receive in the trick or treat spree are G.N.E.R.D.s. While sporting the buff from this candy, your task will be to kill 50 players of the opposing factions. It's easiest to do this in the BGs, where you can kind of hang back and let the HKs flow in.
Check Your Head
Weighted Jack-o'-Lanterns drop from the Headless Horseman, which means killing him regularly will make your life easier. The good news is that since we're all hanging out in Dalaran nowadays, it'll be easy to scout out all the folks you need.
The Masquerade
The ultimate point of Hallow's End is to dress up in costumes. The various wands that let you take on costumes are a gift from trick or treating. You'll need to find other folks who have already gotten their wands, and ask them to hit you with their wands. Once you've gotten all the costumes listed, you're granted The Masquerade achievement.
Sinister Calling
This is the most difficult Hallow's End achievement, since both the Sinister Squashling and the Hallowed Helm drop from the Horseman. You'll have to kill him often enough to have the items drop and win the roll to get the items.
Tricks and Treats of Azeroth
Easy! Simply hit all the inns included in the sub-achievements. This'll supply you most of the items you need in order to get the other achievements, and might get you a bit closer to Explorer along the way.
Summary
Ultimately, the Hallow's End achievements can be alot of work. While they aren't individually too much trouble, they all add up to a couple busy weeks for you. But if you keep it up, you'll utimately become The Hallowed.
