This is a fairly simple, long-term quest. You must steal equipment and items, and fence them. That is, sell the stolen good to the dishonest merchants (fences) provided to you by the thieves guild. Each faction rank requires that a special job be completed, and a specific amount of gold be fenced, before advancement is offered.
- If you cannot find a place to sell stolen goods, speak to Armand Christophe and ask him for information.
- If you are far enough in the thieves guild story, you come across a very unique and spacious wine cellar. You can get a very nice sum of gold for all the wine, and you come across it anyways.
- A good place to steal from is The Copious Coinpurse in the Market District of Imperial City. There are some easily opened locks upstairs, and leading down to the basement. Once you are down in the basement, you should be able to find a few weapons laying on the floor that will push you over the initial 50G fairly easily.
- More good places to steal, ironically, are the imperial city guard towers. Go into one around 2am, it isn't breaking in because the first few floors are open to the public, and go upstairs. In the barracks-level there will be several sleeping guards and a lot of well-priced armor and weapons lying around. Be aware, however, that the equipment is heavy and that it is advisable to have a few feather potions at hand if you wish to carry it all in one load.
- If you are not a member of the Mages Guild, pickpocket the key from a member during the day and come back at night while they are all asleep. There are a lot of soul gems and alchemists tools lying around regularly. If you are a member of the Mages Guild, however, this is generally not stealing and will not help you out.
- Once you get your sneaking skill fairly high, or obtain some constant enchantment (chameleon equipment), castle interiors can be lucrative. Of particular interest are jewelery boxes, which, though almost always "very hard" level locks, contain valuable, light loot.
- You can also try and steal from patrons of Inns after they go to sleep.
- Or, you can do what I did, if you are proficient enough at stealthy things (which considering your guild choice, you should be), whether or not you have done the quest to find the Draconian Madstone for the Countess of Bruma, you can raid her Akaviri collection at night, there are no guards in that area, so you are free to steal away; just make sure you still sneak, you never know. Also, every display box is locked at a very hard level, so I recommend having either the skeleton key, a proper spell, or at least one lock pick, and a lot of patience to reload a save after you lost your lockpick(s) until you get it. It's best if you wait until you get the Madstone, like I did, and I stole it back, selling off the entire collection I had already fenced over 1,000 gold worth of stuff, and that is the most you'd ever have to do, so you can pretty much go through the guild rather quickly that way.
- Other good places to steal are from the homes of NPCs who died in previous quests. Since they're dead, there's no risk of getting caught.
- Another place to go is the armory near the imperial city prison, or the bloodworks in the arena, both have high priced loot.
- Yet another good location to steal is Anvil Castle near Orrin, the blacksmith. Feel free to rummage through the barracks, and cellar. Don't steal from the smith, as he is a member of the Theives Guild as well. Make sure you sneak though, as the guards seem to have dog-like hearing.
- Chorrol Castle has a Varla Stone in an unlocked display case just up the stairs from the main room, which can easily be sold for 500+ depending on your mercantile.
- Drakelowe's basement has a number of high-selling potions. The lady who owns Drakelowe won't follow you down, with no chance of getting caught. Selling every potion can earn you about 1,200 septims.
- Chorrol, Skingrad and Cheydinhal all have rich citizens. Robbing their houses while they sleep is very profitable. Books are usually worth around 20 septims and are lightweight, it's a good way to start off.
- A good way to steal from shops or homes is to use a Telekinesis spell to take items around the corner of a building. If the owner doesn't see you, he/she will not alert anyone.
- One of the all time best places to rob would be Red Diamond Jewelry in the Imperial City Market District mostly everything is below 5 lbs. and are in the hundred septium range it is very easy to gain about 1500 septim from this store at one time...There are quite a few very hard locks and "Needs a key" locks so simply sneak upstairs and take the owners key...Then have fun.
- You could also pickpocket a shopkeepers "key" to his store, then come back at night and rob the place. It takes a good security skill, or loads of reloading.
- A good place to steal from is the weapon shop in Bruma, the lock to get in his store is average and there's tons of valuable weapons lying around on the main floor. He returns home to go to sleep at 12:30 a.m. and there is nothing valuable in his bedroom (upstairs). A fence for the Thieves Guild is a few houses down so its a convenient place to steal from as well. The cupboard off to the left near the dummies, has some clothing, potions, and scrolls in netting you an easy 90-100 septims.
- Get a high value weapon, such as a ebony or daedric one, find a quest essential NPC (one that will only go unconsious), preferably the sparring character in Battlehorn Castle, drop the weapon in front of them, and attack them. They will pick up the weapon. Now, knock them unconsious, and just as they awaken, pickpocket the weapon off of them. It will count as stolen and can easily surpass the 1000 gold needed to start the final quest.