Quick Look: Pickpocket
Your Pickpocket Skill Level determines your odds of success at stealing items from characters. Most of the perks involve making specific objects easier to steal, or making equipped objects stealable. Other perks also increase your odds of stealing successfully further, allow you to poison enemies by placing poison in their pockets, or increase your own pocket management skills.
Pickpocket allows you to borrow things that you happen to have misplaced in the pockets of others. The more valuable/heavy the object, the lower your odds of success. Honestly, this seems like a skill that should have been part of the Sneak tree. Most of the perks are pretty pointless, and the entire skill is a save/load fest. The more patience you have, the less you need to invest any perks into this skill. As for its in-game utility, it’s a nice way to earn a bit of money early on, but rhere are better ways to get money, and you’ll never be able to steal something nearly as good as the items you can simply craft yourself.
Most of the perks in this tree are obviously not worth getting, as they either make already easy to steal objects easier to steal, make stealing easier against sleeping marks, or just give you a higher percentage chance of success. Save/load, you’ll be fine. The only interesting perk - and not for any sort of power-gamery reason - is "Extra Pockets". Increasing your carrying capacity by 100 is a nice boon for a pack rat, and worth about 200 points of Stamina - or twenty levels of attributes. Still, for pure power-gaming purposes, it’s not necesary.
At the beginning, most items are simply beyond your skill, as value and weight determine difficulty. You’ll have to settle for low-value, light items. Sadly, expensive items level your skill faster. What’s a good compromise, then? Arrows. Steal Steel Arrows from various guards. Not because they’re terribly valuable, but because they’re useful. They’ll provide you with a fine stock of arrows in the early-going, and will get you past the first few levels of Pickpocket.
When your skill level reachs about 25-30, you can start targeting more lucrative objects. Gems and jewelry should become your next target, starting with Silver Rings and Garnets, and moving your way up the value ladder until you start being able to nab enchanted items. Save/loading is just a part of the process here, so settle for whatever percentages you can live with and keep your fingers crossed. Plunder the pockets of entire cities and you should level this skill up to max quickly enough. Best part is, you can sell all your stolen gems (provided you don’t use them to level up Smithing!) and jewels to the Thieve’s Guild fences, and disenchant the enchanted jewelry you steal to get started with Enchanting.
|Silda the Unseen||Expert (Lv. 51 - 75)||Windhelm (beggar wandering the streets)|
|Vipir the Fleet||Master (Lv. 76 - 90)||Riften, Thieve's Guide (Ragged Flagon - Cistern)|