I have narrowed most of my progression ideas down, but wanted some input from others. So far I haven't received much. So here are my main thoughts.....
standard monk -> drunken master - while this one is plain, It is also fairly self explanatory for why it would be a choice.
chaos monk -> drunken master (might even skip out on barb....idk) This I feel could fit the general feel of a drunken master with the chaotic side to being drunk. The ability to be confusing on top of being drunk on top of confusing people because you are mimicing being drunk/are severely drunk would give incredible ability to not get hit to top off the flavor of the character.
Unwavering Dedication Monk -> Paladin of tyranny -> Drunken Master - This I would most likely only dip into paladin of tyranny a bit to get the auras, and some of the touch attacks, while focusing mostly on the monk aspects. Seeing as we will most likely be involved dealing with those pesky goody goody cleric and paladins trying to ruin our plots and such, having the ability to recognize when they get near might come in handy, along with dealing extra damage to them from a smite ability.