Estimated Achievement Difficulty: 2/10
Offline: 50 (1000)
Estimated time for 1000: 6-10 Hours
Missable Achievements: None
Glitched Achievements: None
Do Cheats Disable Achievements?: Yes
First off, let me say that the achievements make it look like a lot of playthroughs are needed for this game. However, with this Road Map you'll only need 2 playthroughs max, plus a few chapter run throughs. Ready? Let's go.
Go ahead and play through on Assassin, it isn't difficult at all. Just use cover and curved bullets. It would be best to do the collection achievements on this playthrough as well, the guide can be found HERE.
Also, don't forget to kill the Ex-Girlfriend on the 1st level and the Ex-Boss on the 5th level.
As well, on the last level of the game you can get the "Glad I wasn't there" achievement, "Two is always better than one" and "All in the reflexes". Refer to guide on how to do them.
Run through a second time on The Killer difficulty. It will go by faster this time as you've already been through the game once before. Once you've completed it on The Killer, then the cleanup process can be started. Make sure to get any remaining bullet achievements you need and any rats or collectibles you may have missed.
Clean-up Part One:
Start a new game and go into Time Attack Mode. You can only be on "The Killer" difficulty for this. Now, keep going until you hit the first checkpoint. After your game saves, quit out and go to Unlocked Acts. Chapter 9. Play as Cross. Select "Pussy" mode (it will still be counted as The Killer) and run through it. You will get two achievements at the end for this - "Catch me if you can" and "Between Old Friends".
Clean-up Part Two:
Start a new game and go into Time Attack Mode again. Go until you hit your first checkpoint and exit out to the main menu again. Go to Secret Codes and enter "0100 0011" to get the suit you need. Go back to the menu, Unlocked Acts. Chapter 7. Play as just Wesley. Select "Pussy" mode. Now since we're using the Time Attack Mode glitch we did in the first cleanup, it will still count as The Killer difficulty. Finish the act and you will get the "Heart Breaker" achievement.
Clean-up Part Three:
Start a new game and go into Time Attack Mode once more. You know the drill if you've been following this map. Exit to main menu, Unlocked Acts. Act 3. Play as The Immortal. "Pussy" mode. Run through this till you hit the boss battle. You need to take him out with ONLY a Close Combat move. If you accidentally hit him with a bullet, then get yourself killed, because if you do you will not earn the achievement. Finish The Russian with a Close Combat Move and the "Punishing Subordinates" achievement will unlock.
By now you should only be in need of the achievements that require you to run through multiple times on different modes of play.
Go to Secret Codes and enter:
0110 0101 for Close Combat Mode.
0110 0111 for Head Shot Mode.
These achievements can be earned on any difficulty, so just go with "Pussy" to keep things easy. Start a new game on either mode. Go until you hit your first checkpoint. Exit out to the main menu and go to Unlocked Acts. Chapter 9. Play through until the end and you will get the achievement based on what mode you're playing on. Note that since this is the final level you will be going to, there are no required headshots or close combat moves to be done so the counter will not appear in the upper left hand corner of the screen.
x360a would like to thank v_thorne for this Road Map