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".
