FOR THE KLEPTOMANIACS OUT THERE:
Let’s say we’re attempting to pickpocket something from someone and would like to reduce our chances of failure as much as possible. What is the highest minimum roll and maximum roll reliably possible in the game? In order to make this easier to replicate for others, I’m going to offer some restrictions:
- Things that are not largely guaranteed in most games, such as: Boons, Artifacts, and Manuals.
- This can be any level character up to 20th level, all that matters is that it still remains the highest min and max roll for the check.
- Must be acting alone and receive assistance only from themselves, their items, feats, racial abilities, class features, etc.
These restrictions should ensure that the check can be performed reliably any time it is made by anyone with the proposed build in nearly any campaign with the average amount of magical items and quest rewards, etc.
I will post my own findings as an answer below. Feel free to use it as a frame for further answers, or offer one all your own.