This is intended to be a non-spoiler guide. The first thing to know is that on subsequent playthroughs, on any stage you got a gold prize, you can now simply pause and skip the puzzle. That means get this first.
Golds on all stages means you can skip through and rush to the end. This achievement can be obtained with two and a half playthroughs, saving at the right time.
When you get to stage nine, The Empireo, you'll be asked freedom questions. The answer for 9-1 doesn't matter. Each ending listed below will have three options that you need to pick for 9-2, 9-3, and 9-4 in order to get it. Also, you can get
Whatever, Buddy on either of the two major playthroughs, so they'll be listed on both.
1) Law PlaythroughAnswer only lawfully, your goal is to max out the right side of the chaos/law meter.
Save on the fifth night at the bar!Yes, No, Left Option
Yes, Yes, Left Option
Yes, Yes, Right Option
No, No, Left Option
1.5) Neutral PlaythroughReload the save I mentioned earlier. As your meter should now be maxed to one side, now answer oppositely to move it back towards the center. There's a bit of wiggle room here, so don't worry if it isn't perfectly centered.
No, No, Left Option
2) Chaos PlaythroughAnswer only chaotic, your goal is to max out the left side of the chaos/law meter. If you did not get
Whatever, Buddy, save on the fifth night at the bar!
Yes, Yes, Left Option
Yes, Yes, Right Option
No, Yes, Left Option
No, No, Left Option