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A short, step-by-step guide on how to make easy money in Shornhelm, Rivenspire. There are other ways to earn money, and other places in the town for you to rob, but this is how I usually do it.
Route
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This guide requires you to have the Blade of Woe skill from the Dark Brotherhood DLC, and preferably a few points spent into the Legerdemein skill line. It is possible to complete this without getting caught by the guards, even if you have a bounty.
A small house with an easy lock. Sneak before breaking in. There are 2 NPCs. Pick the pockets of the woman first (2 times) and then use the Blade of Woe to kill her when the man isn't looking. Proceed to to the same to the man, and after that you're free to loot the house. There's a strong box in this house.
Empty house, with an easy lock. Break in and loot it all! No strong box unfortunately. If you have the Timely Escape perk from the Thieves' Guild skill line, a footpad has a chance to appear to the left of this house, and teleport you to safety.
A medium level house, with a harder lock. There are 2 NPCs. Wait for the short haired one to go down the stairs, then pick her pockets and kill her using the Blade of Woe. You're now free to do the same to the second NPC, and then loot the house. A strong box spawns close to the stairs to the unreachable second floor.
Boxes, sacks and barrels in front of the gate. Check them all, as there can be superior quality goods in them.
The Townhall, with an unlocked door. All the stuff in this abandoned house is free to grab, and there can be some decent stuff here although no treasure items.
Sneak behind the cathedral if you have a bounty, or just walk past it if you're safe. This house is the hardest one on the list, but it is also the most rewarding. There are 2 NPCs and they'll be walking all over the place, often facing each other. Look for the right time to pick their pockets and kill them. The woman is the only one who'll walk to the second floor, but the man can sometimes spot her from the bottom of the stairs so be careful. There's a chance for 2 strong boxes to spawn here.
No need to break the lock since the house belongs to a criminal, but she still needs to be killed after you pick her pockets. The house contains some low level loot, but there are sometimes recipes and blueprints to be found. Don't forget to check the kitchen cupboards.
If you have a bounty, you can sneak along the walls of the house towards the crafting area. Jump over the gap in the wall to avoid any guards patrolling the area. Just before you enter the Outlaws Refuge, there are 3 barrels you can loot.
If all goes according to plan, this will only take you 15~ minutes, and you'll get 4000-8000g worth of stolen items, not counting you laundering goods or selling rare recipes. By the time you've sold the loot, most houses will have been reset. If not, just fast travel back and forth once. And if you still have a bounty on you and don't want to pay to get rid of it, the second entrance to the Refuge let's you escape to beyond the city wall to the east, were you can find a safe wayshrine to use.
Source: https://gameplay.tips/guides/2195-the-elder-scrolls-online.html
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