I found an old save game on level 5 that I'm replaying now, since I missed the level 8 neutral/evil achievements. Got the "One Man Scouting Party" and "Data Miner" achievements today, 2 more speech challenges away from "Silver Tongued Devil", ~40 more people to kill for "Doesn't Play Well With Others". 3 more subquests to do, 10 more bobbleheads to collect, and then I go for it.
Scenester: There's a SPEECH exploit that you can use to get the "Silver Tongued Devil" achievement, but be a bit careful when speech challenges come up, try to get as many as possible in the main game.