Overview
Estimated Achievement Difficulty: 4
Estimated Time For 1000: 20-30 Hours, depending on online boosting.
Minimum Playthroughs: 2
Missable achievements: Collectibles
Glitched achievements: Dark Sector - Brutal Difficulty (sometimes reverts to Normal difficulty around Chapter 5)
Offline: 32 of 38 (800G)
Online: 6 of 38 (200G)
Step 1: Normal Difficulty + Collectibles + Enemy Achievements
It's best to get the collectibles out of the way during the first playthrough, just to clear the air a little. Also, the enemy achievements (e.g. Double Decap Latte, Headhunter, etc.) are easy to get out of the way during the Normal difficulty run-through, and the techniques for getting them are in the achievement guide. Also, if you forget to get the Jack the Jackal secret achievement, you can get it on your second playthrough. If you get stuck at all during the story, the achievement guide is basically a great walkthrough.
Step 2: Brutal Difficulty
Now, a couple of people have found that the "Dark Sector - Brutal Difficulty" achievement glitches on them around the completion of Chapter 5. I personally didn't run accross the glitch because I simply beat it a second time in one sitting. If you don't feel like playing the game for 8 hours straight, just make sure that after every chapter to go to the main menu, select a chapter and make sure that it says you completed it on Brutal difficulty.
Step 3: Online Achievements
By this point in time I'm not sure if there is anyone at all playing this online, so I'd suggest heading on over to the Achievement Trading Thread and try and find a boosting partner. The achievement guide has some good strategies for getting these quickly.
[x360a would like to thank prowlerdante for this Road Map]