You need to go in the bar opposite of the South Quarter Entrace. It says "Enter". Go inside and to the otherside of the room. Interact with the guy sitting in the chair for the achievement!
ACHIEVEMENT BREAKDOWN
Est Time for 1000g: 15 Minutes
Required Playthroughs - 1
Missables - No
Price - Only $5.99
Summary - You must solve the 4 puzzles and interact with the correct characters for the achievements.
VIDEO GUIDE