[@Spoopy Scary] I have gone over it entirely and I have a few problems, 
1. I allowed 3 skills, sure you have three but one has three that fall under it, persuade, diplomacy (negotiate), and appraise. If I let everyone do that then everyone would know how to do everything. Separate these three, and then pick 4 (Yes four since I'm letting you level up too) between persuade, diplomacy, appraise, strategy, and knowledge(underworld) 
2. Even though I love all the work you put into this, he seems a bit too powerful in the sense that all he would have to do is walk into a town and someone would know him and do anything for him putting him at way to big of an advantage and not only that but imagine the money intake, he could buy anything. 
3. I would prefer if he was lesser known like the rest of the group, who are just starting out while you seem to already have your life together. It's like letting a level 20 join a level 1 team, get it?