Quest from: Caleb
First let's suppose you want to be with the bad guys. Find Caleb in the docks (N1-2). Talk to him and ask for a job. He'll tell you to get some protection money from a merchant named Hagen (N1-3). When you enter his house, talk to his daughter Reesa and tell her you're here to see Hagen. When you talk to the man himself, you can either reason with him or just intimidate. Both ways lead to the same result, which is him giving the money to you. When you get the money, go back to Caleb. He'll tell the City Watch you're the one they want and you'll have to fight them. When you defeat them, talk to him again and he'll tell you that you passed. He'll mark Moire's hideout on your map.
Speak with Moire / Sweep Through the Docks
Quest from: Caleb / Moire
When you finish Caleb's initial quest, Moire's hideout will be marked on your map (N1-4). Talk to her in there and she'll tell you to go around the docks and corrupt or kill any city watch wandering around.
HINT: There's 600 GP in Moire's hideout and you're free to take it, she apparently won't mind.
You now have to pay a visit to 4 city watch units stationing in the docks and talk to their leaders, trying to persuade them to work for you. It's all a matter of diplomacy/intimidate - if your skills are high enough, you won't have to fight anyone in this quest. Every time you fail you'll have to eliminate a group of city watch. They're not too tough, luckily. When you deal with all 4, go back to Moire.
HINT: There are a few new event appearing on the map this time around, check out (N1-7), (N1-8), (N1-9), (N1-13). You'll also meet Qara near the Sunken Flagon - after the cut-scene you'll be able to join forces with her. She'll be waiting inside Duncan's tavern (check out Qara's personal quest for details on her).
Destroy the City Watch Post
Quest from: Moire
Wanting to enforce her position in the docks, Moire orders you to set the local city watch quarters on fire. She'll give you a torch for that - "arm" with it and go to your destination (N1-5). Use the torch on the two crate piles and a wagon standing by the post's walls. If you're noticed by one of the guards, you'll probably have to fight your way out of here. When all three piles of junk are on fire, just leave the vicinity and you'll see an appropriate cut-scene. Go back to Moire for further orders.
Speak with Axle Devrie / Smuggling Weapons for Moire
Quest from: Moire / Axle Devrie
Despite what you were meant to believe to this point, Moire also has a boss, and that boss is Axle Devrie, who you are now going to meet. Moire will tell you that he is expecting you in the Merchant Quarter (N2-1). Head over there. Once you're in his mansion, talk to Moire again and meet your new boss.
Your goal is to secure a weapon shipment that's going to strengthen your gang in the Docks. Talk to Moire once more and go to the Back Valley (N1-6). You'll meet the smugglers near its entrance. Talk to them and enter the valley itself.
Steadily move forwards through the alley, gradually eliminating the enemies. You can avoid fighting with a group of city guards by going behind one of the buildings near them (1). In order to get through the second post (2) without fighting, tell Neeshka, Elanee or Qara to light something up in order to distract them (the conversation will commence itself once you approach the guards). At the end of the passage you'll encounter a huge band of thugs (3). This time there's nothing to do but fight. Remember to rest and use some positive buffs before the fight. Also, rest afterwards, before it's not over yet. Talk to the warehouse supervisor (4) and go inside with him.
The warehouse has been attacked by the city watch and you have to defend it. For you it means going to each of the (*)-marked points and defeating all the enemies in there. You don't have any time limit, so don't hesitate to rest when you need to. The guards have an irritating habit of appearing out of nowhere around this level, so don't get caught by thoughtless wandering around. After you defeat them all, the supervisor will reward you by allowing you to buy some magical items from him. Nothing interesting, but hey, always a pleasure to search through arcane stuff. Leave through the door in the South-Eastern corner to go directly to Merchant Quarter and visit Axle. He'll send you to Old Owl Well far to the East so that you investigate the matter of a missing emissary from Waterdeep. In there, the two stories - the gang one and the city watch one - will meet each other.
HINT: The only difference between City Watch quest and Axle quest in Old Owl Well is that as a gang member you have to speak to Katrina in there first, she'll give you the papers that you have to show to Callum.