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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.
Joining
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 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
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.