This is a guide from @Greyscales about dear diary.
To achieve Not a total loss achievement,you need to successfully attack and win against the hooded lantern in Chapter 5 using golden arrow or golden knife and you also need to have the ear plugs,then in Chapter 6 go to the weapons table and tell them to use gold weapons.
To get Pieces of the Puzzle achievement you need to successfully choose the correct options in chapter 8 at Jewel Farthing’s house.
A Change of Heart: Capt. Winter will come, and try to entice you to join their side. Do so to get this achievement.
Both Finish the feud and Super sleuth are hard achievements.
To achieve Super Sleuth you need to successfully get maximum bonus in every chapter.
And in Finish the Feud you need to establish peace between temple and tavern.
Here’s a more detailed achievement guide at steam.