Why would that list need more than three things? People tend to not use pickpocketing on their mains because generally speaking, money troubles tend to end about level 4-6, when you start to get a lot of "junk" magic items to sell, and can clean out their gold the easy way.
Most people other than merchants don't really carry much worth stealing anyway. Plus, often merchants tend to be in areas with lots of people, making them difficult to pickpocket at all.
The good news is that you can indeed pickpocket the same person with two different characters. There's no general "has been pickpocketed" flag that applies to everyone, it's a "has been pickpocketed by Wolgraff".
Because! Bro, I'm really slow when I play games like this... And I guess if other players are as slow as me, they'll notice that the skill book lady in Homestead actually sells the books AGAIN, before even leveling up! I've "had to" buy 4 books already since I leveled up to level 10. It adds up man! Seriously, especially if you buy every shiny thing you come across anyway. I gotta tell you, I'm a complete scroll and special arrow junkie. I've probably spent 30k+ on that stuff this playthrough and I'm only at level 10. I also buy weapons and enchanted gear all the time whenever I see something that gives 1 attribute in a better direction.
I've been making my money selling beer and loot but it's getting to the point where I'm going to NEED to pickpocker next level to buy as many skill books, unless I want to resort to cheap explotative crafting tactics (a la Elder Scrolls - no thank you). You see, from a roleplaying standpoint, pickpocketing makes sense. However, crafting overpriced potions and ridiculous weapons only to sell them en masse to everyone from painters to Vegetable merchants, is less realistic, and starts to bother me and I feel like I'm back in Skyrim where I made 20k in like 5 minutes of enchanting daggers.
I've used pickpocket on my main with some success through this playthrough. Since this game isn't so hard that you need to min/max, it didn't hurt me to throw 3 points into pickpocket. That + gear already worked for some funding. Now, however, everyone in town is starting to carry some serious money, so the time has come for Wolfgraff to make the rounds with a high pickpocket. =) I'm not interested in using Wolfgraff or the Ranger lady at all for my main party. One of my two mains is a Ranger so I'm fine and I've grown attached to Madora and Jahan. I might as well get some use out of those other 2 now.
