- Estimated achievement difficulty: 4/10 [Achievement Difficulty Rating]
- Offline: 53 
- Approximate amount of time to 1000: 30-35 Hours [Estimated Time to 100%]
- Minimum number of playthroughs needed: 1 [with save/reloads]
- Missable achievements: Many [28, see roadmap]
- Does difficulty affect achievements: No
- Unobtainable/glitched achievements: No
Next, take great care in reading each chapter's road map overview fully before diving in. Many of the chapters are linked very closely and you must do one action in one chapter and complete it in another. At the same time, individual chapters will have branching options and you'll need to save/reload inside the same chapter to get both choices complete - but be wary of which final choice you go with so you can ensure the best outcome later on.
Lastly, if you recruit any of the characters from previous chapters (which you should, they are very powerful and will have their entire inventory available to you, including weapons, bandages, lockpicks, Nimp Relics, and Golden Aces) make sure they do not die. There is an achievement for making it to the end of the game with all of the story characters alive. Also be wary of the NPC Essex Mast who can also die and is needed for multiple achievements late in the game.
As for the game's difficulty, that's up to you - but feel free to play on Story difficulty as no achievements are tied to playing the game on any higher difficulties.
Step 1: The Bounty Hunter
When you get to Quickbend in the story, make sure to release Essex Mast from his cell so he will be alive later in the game. There are two mutually exclusive achievements in this chapter. You will want to save when you get to your husband in the Quarry to rescue him and obtain Out on the Ebb Tide (15G) first by killing Shelby, then reload your save and get The Great Escape (15G) by ignoring Shelby and have this be your official choice.
This chapter is a great one to work on as many of the game's random miscellaneous achievements as possible, and start working on doing side-quests, reading books, etc. There are a lot of achievements where you'll want to save prior and then reload, such as going to jail, stealing, killing an entire town, etc. You should be able to knock out nearly all of them before moving on to the next character.
Step 2: The Pigman
Before completing the chapter, ensure you have done the "Bard's Bargain" side-quest which is given automatically after during the story at the Pit. At the end of the chapter when speaking to the tree, choose to free all the Pigmen. Doing these two things will setup the ability to play poker against Pigman Joe for Hog Wild (15G) starting next chapter. Not doing either of those things will not allow Joe to show up.
Step 3: The Protector
When you arrive in Heronwall Summit for the story you should find Essex Mast here, once again confirming he is still alive, and ensure you get the book from the scholar for him. Make note of the achievements Fallen Star (15G), Healing Old Wounds (15G), and Hog Wild (15G). Since we turned Ruth into a pigwoman last chapter, she will be available as a bounty for Monster Hunter (15G).
Step 4: The Werewolf
During the story when you return to Absolution Hall, you should find Essex Mast talking to Franciscus, once again confirming he is still alive. It is at this point you should get the Trapping Souls side-quest to unlock The Philosopher’s Stone (15G). At the end of the chapter, make sure you choose to destroy the blood moon so you can recruit the werewolf in the last chapter.
Step 5: The Oneirist
You'll also need to unlock Mystery Machine (15G) (make sure you don't decline this encounter!), Explorer (15G), Winter Has Come (15G), Who You Gonna Call? (10G), and Eternity Can Waits (10G) during this chapter - this should be the final confirmation that Essex Mast has survived the entire game.
Once you reach the end of this chapter, there are two separate achievements for the ending. An auto-save happens right before the choice, so you can answer with feelings for There is Hope (90G) and then reload and answer without feelings for It All Dies (90G).
Step 6: Dirt and Blame / Clean Up
[XBA would like to thank The Pants Party for this Roadmap]