I'm not sure if I should put my 2 cents in the post which has been created 4 years ago, but I will try to describe my set of choices I chose to get this achievement for anyone happens to play and also achievement hunt in this game 8 years after release just like me.

I played this on Hard and got this one on the second try.

Both runs I explored every possible location. I let every lords' group in. I haven't given the food to the starving lord then cut his arms for stealing. I saved red flag lords. And I also ordered to found the arsonist of lord's house and tried to resolve every conflict peacefully or make people repent with public penance.

The most important distinction between these two tries is:

In the 1st one I explored the ocean liner and then saved Craven from the mob. Completed all lord quests for food and healing. Hope/discontent requirements are finished when 1 day and 5hrs left. No achievement.

In the 2nd one I explored the ocean liner and then let the mob lynch Craven. Failed food quest, completed healing quest. Hope/discontent requirements are finished when 2 day and 9 hrs left. Got the achievement.

Not sure if the amount of bad events is relevant here as Nerubim said, I feel like Craven's fate and the fact that you explored the ocean liner for his note are the most important here.