Step Three: Getting In
Sneaking and Lockpicking are your friends. Sneaking allows for discreet night time action and serves as the gateway to Pickpocketing. Even when you’re in partially visible light with people moving around, provided you keep still, you’ll evade detection. As many homes and structures face the guard-friendly paths you want to stay off, travel by rear perimeters and infiltrate by rear entrances whenever possible. Remember, if you’ve done it right, you’re going to be entering these homes while people are (hopefully) sleeping, you’re going to need to be silent. Nothing like waking a shopkeeper who’s sleeping with a mace. It only takes waking them up and getting into a fight to summon the guards, after which bad things will happen.

Step Four: Prioritize Your Targets
In the world of Skyrim, it is super easy to get trapped by ambition. You see a table full of candles, set plates and food, and you instantly think “Mine!”, but avoid the temptation. My rule of thumb on good items is that their value should be roughly 10x their weight. So if a plate weighs .5 pounds and it’s worth 5, that’s a 10x multiplier. Anything less than you’re wasting your time, this goes for heavy stuff like pots and pans as well as heavy iron armor and shields (shields are generally 12 lbs and worth 60, not a good play). Another reason is that it’s easy to burden yourself when you make it up to the sleeping quarters and find fancier stuff like jewelry. Nay, being mid-raid is not a good time to be tossing out the silverware collection you thought would look so good in your inventory. Wines and cheeses are a good thing to stock up on, especially in humble residences. Once you’ve sacked the place, exfiltrate with care.
If you really want to get some good stuff, you need to get your Lockpicking up and make sure you have a good number of picks on hand. Thankfully, the game utilizes the great pick system from Fallout 3 which uses both sticks (if you’re on a console). If you’ve never messed with it before, it goes like this: the sweet zone is going to be an ever-narrowing slice of the pick zone depending on the difficulty of the lock. Once you’ve found a good slice to try, you can then try and force the lock. Never force the lock, always turn gently as to not inadvertently destroy your picks when you can still use them to survey for sweet spots. If you have your pick in the wrong zone, it’ll snap and you go at it again, if you get it right, the sweet cache inside is now yours.
Step Five: Rinse And Repeat
You just found the place, it’s time to hit up the next building and continue your tour of terror. You’ll be able to off-load much of your stolen cargo to that general goods vendor you hit up first, so this is all good starting out. But, there’s be a slowly growing stockpile of phantom goods that you can’t pass off to mere mortals because of their, well, not yours status. Enter Step Six.

Step Six: Get Your Butt In The Thieves Guild
As clever as you’ll feel knocking off your first few villas, you’re just not going to get very far without the help of the Thieves Guild, which not only includes cool, exclusive items, but also allow you to sell off your stolen wares through the guild’s fence, too. Without spoiling too much, you’re gonna need to get your keester over to Riften (in the southeast corner of the province) and complete a series of quests for them to gain their trust and access to their facilities and personnel. Once you’ve gotten that down, you can then help the guild expand its influence to other towns as well. Why is this the last step? Honestly, because maybe you’re not up to the life of a good thief. Pedestrian theft of jewelry and that is hardly a way of living, you need to put all goods on the table if you’re gonna make it in this harsh realm.
Well, all the best of luck to you, my fellow thieves. If you have any hints or suggestions, be sure to drop them in the comments below or throw them in the forums for discussion, too!



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