Smuggler's Run

Background
Upon entering the city of Amaranthine for the first time you will come to a NPC called shady character. he will begin talking to you about your reputation, if your interested you can follow him and speak with him further. there are 2 distinct paths you can take with this quest line. you can help the smugglers or you can help the city guard. you can only choose one side. the only side effect i have found is if you help the smugglers the city guard will take to you rudely if you select them.

He will tell you there has been some trouble with trade in the city and through his help and the other smugglers you will be entitled to a cut if you help out. After speaking to the shady character you will learn he wants a small favor, the local bartender has a secret passage and he is trying to extort more coin, the smugglers want you to persuade or intimidate him to open the passage. after dealing with the bartender and speaking again with the shady character you will learn that there are some thug that are getting in the way and if you will deal with them you could earn more money.

Upon speaking to the smuggler leader he will thank you for your assistance in dealing with the unwanted guests, Continue talking with him about why he is down in these caves you find out he and his men are responsible for bring goods and supplies into the city for the people in need. He will then ask you to do one more favor for him the city guard has been causing problems he wants you to take care of the Lieutenant. He tell yous the Lieutenant should be in the Guard house and one of the city guards should have the key.

After Obtaining the key to the guard house you will find a Jacen A Elf that claims to be the Finest Best archer in the whole arling, If released you can have him fight at vigil keep.

Walkthrough
This walk through will assume you want to help the smugglers if you want to help the city guard then see this quest guide Law and Order after your encounter with the shady character head to your left down this walkway soon as you can turn right do so. you will see the shady character speak with him.

Head over to The crown and Lion Inn and have a chat with the bartender, after you persuade or intimidate him head back to the shady character. After talking with the shady character again head into the house next to him and enter the passageway. Upon entering the secret door you will have to fight a bunch of thief's. after defeating the thief's a group of smugglers run in speak to the smugglers leader. after talking with him Head out of the caves the easiest way is to exit the other side of the cave from where you entered. you will find yourself inside the Crown and Lion Inn. after leaving the Inn you need to go to each of the battlements you have quest markers, one of the sergeants will have the Guard house key. Upon looting the key the quest will update. in the north side of the city you will find a door that leads to a Guard house use your key to enter.

Upon entering you be confronted by the lieutenant you will need to fight him and his men. after killing the lieutenant and his men loot his body you will find a cell key go around to the back of the guard house and open the cell door there is Jacen A Elf in a cage. if you choose to release him he will gladly head to vigil keep and fight for you. after you are done dealing with Jacen, collect your loot from the various chest's and head back to the Smuggler's leader.

Result
10 Gold (First reward) (A key to the secret door in the house next to shady character) 15 Gold (Second reward) Nathaniel disapproves -1 20 Gold (Final Reward)