Yes you can steal some pretty awesome stuff including suits of armour etc. You need to assign points to your pickpocketing skill to steal from shops etc. You can use various potions such as Master Thievery or perception etc to increase your chances. You can also use and equip items such as the Gloves of Pickpocketing to increase your base score. dexterity is the most important attribute for thieving and removing your armour will assist in thieving. generally I've found that with a pp skill of around 165 - 170 you can pretty much steal from any shop without trouble. Bernard in the Copper Coronet is a notable exception, I've had 250 in pp and still been regularly caught by him. Thieving from thieves can also be a risky business. There is always a 1% chance that you will be caught regardless of your pp skill.
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It's bleedin dark down here, slippery too.
Man, that's a pisser.
