The Elder Scrolls IV: Oblivion/Thieves Guild

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Thieves Guild

Overview
Heavy armor not your thing? Prefer stealth to violence? Like to steal shiny things? The Thieves' Guild is the perfect place for you. The guild quests mainly consisting one thing or another from some unsuspecting sucker without getting caught. It also encourages you to rob people on your own and sell your stolen items to special guild vendors.

Tenets
Every guild has tenets that you must follow and the Thieves' Guild is no exception.

Tenet 1: Do not steal from any guild member.

Tenet 2: Do not kill any guild member.

Tenet 3: Do not kill anyone while you're on a guild quest. This is the trickiest one because even if they attack you, you still aren't allowed to kill them. If you do though then you get into the Dark Brotherhood without getting arrested.

Getting Back In
So you broke the rules and now the thieves are mad at you eh? Well as with any good thief money fixes anything so the first time you get kicked out of the guild paying Armand a thousand gold is enough to get back in. It's a bit difficult since you can't turn in stolen loot, but you'll manage.

Joining
The Thieves Guild does not have branches open to the public in the same way as the mages and fighters guilds, so joining is a bit trickier then other guilds.

Method 1: JailBird
To join the Thieves Guild you will first need to accumulate a little jail time. So steal something in the imperial trade district and go to jail when a guard catches you. After your release visit the waterfront district and a female dark elf (Dunmer) should give you a note with where to meet.

Method 2: Ask the Bum
Alternatively you could become good buddies with the beggar in the waterfront district. You'll probably have to bribe him a little. THen ask him about Gray Fox and he'll tell you where the meeting occurs.

The Meeting
For those of you who are too impatient to have to treat this like an actual quest. All you have to do is meet behind one of the houses in the waterfront district at midnight. Just walk around at around 11:30 and talk to the guy with the torch.

Quests
The Thieves' Guild quests are mostly consisting of stealing specific items from targets. Many of them require you to avoid detections or if you do get detected run away. Remember you will be expelled from the guild if you kill someone you're supposed to rob. We're thieves not muggers.

First Quest: May the best thief win
Upon talking to Armand at midnight he'll say that he's surprised to have 3 recruits at once (there is a Wood Elf and a Argonian are with you as well also trying to join the thieves guild.) He decides to make it a contest and sends all three competitors off to steal Amantius Alectus's diary. He also tells you that you can't kill the other thieves so all you blood thirsty people be warned.

Now you probably have no idea where this guy lives go walk a few feet and you should see the beggar sleeping on a blanket outside. Wake him up and if your buddies with him already (you should be since it's how you join the guild) he'll tell you exactly where your target is and put it on your map.

Now race there completely ignore stealth til you get there. When I did this quest the Wood Elf beat me there. If it's possible to beat her there someone please edit this. BUT don't fret all is not lost. We're trying to get into the Thieves' guild so do what any good thief would do, steal it back. Wait/Sleep until the morning and go back to the waterfront and find her house. Pick the lock and head on in. She should be sleeping or out and about it doesn't matter. Pick the lock on her chest and steal it out from under her nose. Wait/Sleep until midnight and turn it in to Armand for the quest reward and entrance into the Thieves' guild.

Freelance Work
Now before Armand will give you the second quest you need to sell some ill-gotten goods to a guild member. Now that you're a member of the thieves guild you can sell all that stolen property thus stealling from people actually means something. All quests from here on out will require some kind of money requirement. Example: Before you're assigned the second quest you must have sold 50 gold worth of stolen goods.

Personally I suggest robbing the imperial bookstore. I've yet to do it myself, but while I was in there I couldn't help, but notice so many books worth 10 that weighed next to nothing.