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To any players with thief characters, tell us of your best accomplishments, your biggest heists. :3

I joined the thieves guild. Used my journeyman speechcraft to manipulate the countess of Chorrol to allow me to do the investigation = free access to most part of the castle.
I made off with every last piece of silverware and many gems and some valuable books. And after I revealed to the Countess about the quest (spoilers not gonna tell) I got some extra cash and gems without her knowing of my burglary. :3 I strutted out of Chorrol with a bag of goodies and a grinning smirk.

There really isn't anything worth stealing besides food. Even in castles and upper-class homes. Sure you might find a jewelry box or two, but they don't respawn. And most chests, even those locked with very hard locks, will most likely only contain clutter.

Since there is nothing worth stealing other than food, I had a great time robbing the entire town of Skingrad of every last scrap of food once, and all in one night (COBL time scale rocks) like the Grinch Who Stole Christmas. Then I brewed well over 1,000+ Restore Fatigue Potions and sold them to Sinderion.

Now imagine everyone waking up to find not a single bite of food ANYWHERE, and their only source of nourishment are 1,000+ little pink bottles of liquid. Now imagine what an all-liquid diet would do to a person's digestive system.

They'll be having the squirts for weeks, and my wallet grew three sizes that day.

I also did this to to the Talos Plaza District once too. The Inn there is a great place to hit as the 2nd floor is full of food and not a single NPC goes up there except the one involved with that Skooma addict and she only shows up during that one Dark Brotherhood quest I think.

My ultra-efficient gameplay for a female Breton weakling has her doing the thieves' guild initiation the second night out of the sewers (I spend the first night in jail after stealing an ink well from Edgar Vatrine to get arrested - I must go to Edgar to buy his 'Ease Burden' spell). I start the TG test at midnight and then fast travel to Bruma, strip naked and try to steal $1000 out of the Bruma mages' guild 1st floor in one shot before Jeanne Frasoric wakes up and comes downstairs to start the day. If there is Boar meat ($20) in the pantry I can make it in one trip (fenced to Ongar at 48%). If not, I usually can't carry the last few items needed to top $1000 and I have to steal the rest from under Jeanne's nose. I never have to steal/fence another non-quest item from that point on, and I have enough cash to buy a couple of grand soul gems and destruction spells to make my first enchantments later. From Ongar's, I go back to the guild house, put on my clothes, join the guild, and then legally strip the rest of it of valuables (the Glow Dust is needed for the Azura's shrine/star quest.)

With the Tower Stone spell "open hard lock" and the 'open very easy lock' spell from Alteration Major Skill, (IIRC) I can do it all without picking a lock. (The Tower stone is straight across the bay from the Waterfront fast travel point.)

I robbed the entire Imperial City market district in one night. I had completed the Thieves guild Quests, and become the Gray Fox, so I wore the Cowl, snuck around in the shadows, used the Skeleton Key, and made off with every single thing of value in every store. I even managed to, after a full hour and a migraine, rob the Feed Bag and The Merchants Inn. I used invisibility to avoid the Watch. The sun was just coming up when I was done and, hello sun damage. I was still working on the cure for vampirism. You would not believe how hard it is to get Nightshade sometimes!!

Nightshade grows like a weed in the West Weald. A ton of it grows in the forest and hills between Skingrad and Bravil.

I hate scouring the countryside for alchemy ingredients though, and the apothecaries are practically useless for supplies as they only carry one or two samples of ingredients.

So I picked up this mod:

Now every apothecary sells ingredients and potions by the dozens. If I need to stock up on healing potions before jumping into an Oblivion Gate, I just pop into town and buy 20 Cairn Bolete Caps and 20 Lady's Mantle Leaves and BAM! I am set.

It does break the game as merchants also start selling food by the hundreds. Buy 200 Blackberries and 200 Strawberriess for 800 Gold. Make 400 Restore Fatigue Potions and sell 'em back to the merchant for 10,000+ Gold.

It might have been Chorrol, I wasn't really paying attention, but I had to steal the countess's ring. And not only did I steal it, I stole it as she stood there by her bed, her husband (I presume) already asleep, she putting the ring in the jewelry box. I had to check her 3 times for it to see if she had dropped it yet, never catching me in the process, and when she finally did and I moved forward to "claim" it, I was technically IN FRONT OF HER to open the chest.



That was when I learned the power of Sneak. Oh yeah!