One quick thing I want to note. If you're playing with a good group of people, make sure the drummer is on expert and not expert plus.
The first few times I tried for this it wouldn't pop for me, and I couldn't figure out why. Everyone seemed to be on expert. But, I later found out that the drummer was set on expert plus, which will break your chance of getting this even if you don't play an expert plus enabled song. The next song I did, making sure the drummer was on expert, popped the achievement.