The Warlock promotion quest is by far the hardest promotion quest in the game. I advise against having a Druid if you know you're going to choose the dark side, unless you like a serious challenge.
I generally do a single party (of a knight, an archer, a cleric, and a sorcerer) and save my game when the time comes to make the big choice. First I do one, then I go back to that save and do the other.
Since you've finished the game once already, you know which promotion quests on the neutral and good side are easier than which. Don't short-change yourself by including a class with a particularly tedious (to you) first promotion quest, again unless you like the challenge.
Post edited March 17, 2011 by Paviel