An easy guide to getting the second most elusive achievement.
Preparations
Before you embark on gaining this achievement, make sure you do the following:
Send away followers
Followers can be a big problem when you gain your 1000 gold bounty, especially if they’re noble, and are likely to turn against you if you kill innocents. By dismissing them, you no longer have to worry about being backstabbed, and they can’t block vital exits when you need to take your leave from the crime scene (Yes Lydia, we’re looking at you)
Equip a melee weapon (or two) and level it up
When you are in the process of gaining your bounty, a bow is the most inconvinient weapon to use. It takes time to load, fire and reload, alot more time than simply swinging your sword, or axe etc. By using the sword, you can successfuly gain your bounties and defend yourself when the guards come calling- but make sure you’ve levelled it up suitably (your one handed/two handed skill) and make sure you use a good weapon-dragonbone or daedric are best) or you’ll be in for a nasty suprise when you attack someone.
Equip good armour
Same as sword really. Good armour means you won’t be killed quickly, so you can flee without being snuffed out with a guard’s iron arrow.
Have lots of health and stamina potions
The health potions speak for themselves; when you commit a 1000 gold crime, the guards will attack you, and naturally, you’ll get a little scuffed up. Having the health potions means you won’t need to eat a dozen cheese wheels in the heat of battle, and means you can recover from devestating injuries with ease. The stamina potions are vital to the escape; in order to get the achievement, you need 1000 gold bounty in all holds simaultaneously, and the only way that can happen is if you live to fight another day after you complete each horrific crime in each hold. The stamina potions ensure you can run away at haste, without having to take a breather, in which time guards could catch up with you.
Make sure you can fast travel to each hold.
After slaughtering the men and women of whiterun, do you think you’ll have time to hop on a carriage to winterhold? No. Make sure you’ve travelled to each hold capital before you begin your crimes, otherwise you’ll waste a large portion of time having to walk to any holds you haven’t discovered yet.
Finally, SAVE before you begin. Then Save again, and again…
I cannot emphasise the importance of saving before you go on your crime spree. Unless you want to live the remainer of your skyrim days as a wanted criminal in each hold, make a save file in which you wll commit your crimes. That way, you can simply return to your original playthrough after you’ve successfully become public enemy #1 in Skyrim.
The crime spree
To gain the achievement efficiently, and safely, I would recommend the following order through which to commit your crimes:
1. Winterhold (Winterhold)
By far the easiest hold to gain your 1000 gold bounty. To gain the bounty, simply fast travel to Winterhold, wait until daylight (best time is around midday) And kill a guard. Then wait for reinforcements to come, and kill a second guard. The more brutal, the better. However, when you murder in Winterhold, make sure you leave at least one witness alive, otherwise you will forefeit the bounty as all witnesses will have been killed. Don’t bother trying to get the bounty in the college of Winterhold. You’ll be blown apart by the mages there, and even if you do survive, you’ll still have to flee across the bridge, where guards will await you. When you’ve run far enough to fast travel (when enemies are no longer nearby), save, then travel to…
2.Falkreath (Falkreath)
This ones next because, like Winterhold, the hold capital does not have a seperate ID, and so there is no loading screen to escape. To gain the bounty here, again, murder the guards, or civilians closest to you, and again, leave at least one alive so you don’t forfeit the bounty. Once your murder spree has finished, run far enough to fast travel, save, and head to…
3.Dawnstar (The Pale)
Repeat the stages of Falreath/Winterhold here. Guards outside the inn, at around midday, are your best bet to gain the bounty.
4.Morthal (Hjaalmarch)
Repeat the stages of Falreath/Winterhold here. Best place is guards/ civilians outside the log mill, across the bridge, to minimise the reinforcements sent. Again, ensure witnesses are left alive.
5.Windhelm (Eastmarch)
Things get a little trickier now. The best way to gain the bounty in Eastmarch is to enter Windhelm after dark, and proceed to kill th guards and civilians that linger at this time of day. Once your crimes are committed, flee Windhelm, and put enough distance between you and your pursuers to fast travel to…
6.Riften (The Rift)
The Rift is hard simply because most of it is so sparcely populated; save Riften itself. The bounty here should be generated by murdering the individuals inside Riften, not the guards outside. The only exception to that rule is if the Khajiit have parked outside Riften; in which case kill away. This is the easier option, as there is no loading screen, but either is fine, as long as you are prepared.
7.Markarth (The Reach)
Enter Markarth and murder the individuals in the stalls to the right of the entrance gate. Immediately leave Markarth: Guards with bows here are more dangerous than other holds, as they are positioned on the birdges in Markarth, which act as vantage points. Once enemies are no longer chasing you, head for…
8.Solitude (Haarfingar)
This one is hard because of the sheer density by which the citizens live in Solitude. The difficulty in obtaining a bounty in Solitude comes from the actual escape, as oppose to the crime. The best way to obtain the bounty is to attack (and kill) several of the citizens and guards making their way to the hold capital up the road to Solitude. Leave witnesses, but by not entering the city you make your escape alot easier than killing inside Solitude.
9.Whiterun (Whiterun)
By far the hardest hold to gain a bounty in, ironic for the level at which the player will first encounter Whiterun city. Attacking inside Whiterun city (which I know you want to do because that’s where Nazeem hangs out) Will mean dozens of guards spring on you instantly, and, een if you do successfuly flee, mor guards await you in the surounding farms and land. However, this bounty is alot easier to achieve than others, providing you left it last. This is because to get the achievement, you only need to get the nine bounties, not get them and escape. Therefore, to gain the bounty in Whiterun, head inside Whiterun city, kill some people there, and hey presto, the achievement is yours.
Now, revert back to your first save and enjoy a crime-free Skyrim experience (for the time being, anyway)