Good for bribing guards once you've killed everyone and the perk you said. It'd just my preference if I went assassin. It's true what they say though, "Keep your blade sharp and your tongue sharper."
I plan on joining the Thieves' Guild, which adds a kind of bribe option on default. Pay the money, then pickpocket it back. And as a real assassin I don't plan on getting caught

Thanks for the input though!
You could switch illusion or smithing to pickpocket! It is very easy to level up and you'll become rich very fast!
I plan on using Illusion to keep it fresh, but I might invest something in Pickpocket. I have some points in Pickpocket on my current main, and it works well to earn some easy money and weapons. Thanks for the input
