You will need to receive a bounty of at least 1,000g in each of the nine holds it doesn't have to be exactly 1000 it can be over that amount, but the bounty in each hold needs to be all the same time, you cannot get your bounty pay it off and then go to an other hold. Will suggest to make a save and then go for this achievement unless you don't mind paying the bounty later on and most importantly not having an NPC die from your hands that you might need later on for a quest.So save and when achievement pops reload.