First of all, you should put at least 3 skill points (lvl. 2) into Barter, so you can have 4 total with gear. This is a MUST. In fact, might as well do it in character creation. Just think, that with even 1 more skill book you can afford you get those 3 back already.
Mini-Guide for Pickpocketing:
Intro: Why pickpocket? Because it's fun!
1. Get invisibility. (Walk in Shadows) or the AL2 Aerothurge one.
2. If you don't have invisibility , get Make Invisible (AL 4)
3. If you don't have either of those, get them. - Why? It's gonna take 10x as long to make the rounds if you're gonna have to be distracting guards with conversations and stupid things like that every single time. If you seriously can't get it for some reason, then forget pickpocketing normal people and only focus on Merchants.
4. Never steal from a Wizard/Mage. They will kill you. That goes for Arhu, Evelyn, Theon or w/e and every other crazy cat in town. Exempt: the Withcraft Merchant in the Inn and in the Market are game.
5. Quick Save every now and then!!
5. Get pickpocketing level 3 minimum, 4 better, 5+ optimal. Anything below 3-4 isn't even worth the effort. Remember there's 2 pieces of gear that can get pickpocket.
For merchants, you can begin right away at the start of your game, because they're loaded.
For normal people around town you should wait until level 10+ for them to have anything even worth stealing. You may see only 100-200 coins but usually there's an item also. MANY people have small healing potions too. It adds up. Grab a potion, some gear, scrolls they have have and their cash and it's a decent loot for 1 second of your time. Another thing is you often get things that seem to be of little worth but aren't. A special Arrowhead worth 60-120 is made into a special arrow of twice that value. Anyway, with invisibility, you can pickpocket like 5 people before next cooldown, and the cooldown is pretty quick. In fact, it must be even quicker for the Aerothurge one if you have high INT but I don't have that one so I'm not sure.
