Next of Kin (Oblivion)

Overview
Faction: Dark Brotherhood Quest Giver: Dead Drop Orders #2 Reward: 500

Background
Your objective is to eliminate the entire Draconis family, five targets in total. The only information you have to start with on this mission is the location of Perennia Draconis, the mother of the doomed family. She is located at Applewatch farm just west of Bruma.

Perennia Draconis
Head to Applewatch and speak to her. You must extract the location of her children and then kill her. The best way to do this is to pretend to be the shopping service she has hired to send gifts to all her kids. She'll generously give you a list of all the other Draconis family members as well as 100 gold for the errand. Kill her and then move on. You could also kill her and take the list from her or let an enemy kill her.

Caelia Draconis
Caelia Draconis is a city watch guard in Leyawiin who works the night patrol. Unfortunately, she doesn't appear to have any moment of vulnerability you can exploit. She is rarely alone and is always armoured. Any attack in public will of course leave you with a large bounty, not to mention a great deal of trouble from the other Leyawiin guards. The best time to take Caelia out is just after she finishes her watch at 7 am. She will go to a private room upstairs in the Three Sisters Inn. Here it is possible to engage her one on one. A one shot kill here is difficult due to her being fully armoured so you will likely pick up a small bounty regardless. One way of avoiding the full 1000 gold whammy is to whittle her health down to a small sliver and then use a poison attack with a long duration. Do your best to avoid her until she succumbs to the poison. This death should only leave you with the 40 gold bounty you picked up for the initial attack.

Another option to kill Caelia without getting bounty is to get her into a place where it's just you and her. Don't mind the civilians because they won't attack anyway. Then, if you are a Conjurer, summon Dremora and attack it three times. This will make wild, attacking both you and Caelia. Just run and let Caelia attack the Dremora. After a few hits, the Dremora will fight Caelia. Just summon more Dremora and attack them a few times until the Dremora eventually kill her.

A third alternative for not getting any bounty is to use a Frenzy spell, provided that you are skilled enough in Illusion and have a potent enough spell. Once cast, she will attack you first, and you have every right to defend yourself.

Yet another option is to get practically 100% Chameleon through any means, and strike her down. You might or might not get a full 1000 gold murder bounty, but it's possible to avoid it since they cannot find you.

Note for the conjuration option: you can't provoke a fight and whittle her down, and then use the Dremora strategy to avoid the blame: you still get hit with the 1000-gold fine even if Caelia is fighting to defend you when she dies, if you did most (any?) of the damage.

Another option is to talk to her and say that you need her dead. She will follow and attack you. Run out of the town to the Oblivion Gate and jump into it. Jump over the damaged bridge and she will fall into the lava and die. Move out of the Gate and travel to Waterfront where you pay your fines of 20 gold.

Lastly, you can wear the Gray Cowl of Nocturnal if you have it and kill her as usual. The Gray Fox's bounty will go up, but your character's won't.

Andreas Draconis
Andreas always has a guard posted in his room, staring almost directly at him, at all times, with no breaks. This makes it almost impossible to simply kill him. However, there are several ways to trick him into attacking you, at which point you can defend yourself. Simply talking to him and saying that his mother bled like a pig is the most direct way. You can also use a Frenzy spell. Should either of these count as a crime in any way, try lowering his disposition to 0. (Enter the Speechcraft minigame, and either deliberately fail at it by matching the large wedges to the options he hates, or simply not pick anything and stare blankly at him as his disposition slowly falls.) He is very aggressive, and will attack you simply for not liking you.

While the constant guard presence makes him almost impossible to assault without an alarm, the guard proves to be his undoing if you get him to attack first, arguably making this the easiest kill in the entire mission.

Another way of killing him is to wait until he is asleep, and then perform a sneak attack for a one-hit death, behind the counter. If done correctly, the guard will not see you and you will receive no bounty.

Yet another way is to simply sneak to the steps behind the guard, arm yourself with a good bow, poison your arrow with a paralyze/damage health poison and shoot the guy. This will knock him out and he will die quietly. The guard will do nothing as long as you remain in sneak mode.

Sibylla Draconis
Sibylla Draconis lives in Muck Valley Cavern with her surrogate family of wild animals. This kill is straightforward and you should approach it like a standard dungeon crawl with a boss. There are no witnesses other than her mangy (and probably dead) crew so you don't have to worry about any nasty bounty this time.

Matthias Draconis
The final family member can be found in the Talos Plaza District of Imperial City. Matthias Draconis is asleep upstairs in his house from 12 am - 5 am. Pick the lock to his door and end him.

Pick up your reward and new orders at the next dead drop in Skingrad Castle courtyard.

Trivia
Andreas Draconis of the Drunken Dragon Inn suggests that you go to the Inn of Ill Omen or the Tiber Septim Hotel instead. Both of those inns are involved with a Dark Brotherhood quest.

If you return to Applewatch sometime after completing the quest, you will find the tombstones of all five Draconis members, with a personalized epitath for each, and Caelia's sword leaning against hers. If you read Perennia's headstone, its epitath is somewhat threatening ("Here lies Perennia Draconis -- May her spirit forever curse the murderer who stole her precious life") and reading it causes her ghost to spawn directly behind you and attack. The ghost is extremely weak and should not pose a threat, but it can be startling. (Or it might just blatantly scare you).

Journal Entries
Upon receiving the quest:
 * I have received my new orders from Lucien Lachance. I must kill every member of the Draconis family -- Perennia Draconis, Matthias Draconis, Andreas Draconis, Sibylla Draconis and Caelia Draconis. I know the location of only the family matron, Perennia Draconis, who can be found on the farm known as Applewatch. I should head to Applewatch, find out as much information as I can on the locations of the other family members, and then systematically kill them all.

After speaking with Perennia Draconis:
 * Perennia Draconis has given me a document that lists the locations of all the members of her family. She thought I was the delivery person she hired to buy gifts for her children. I will instead use the list to find and slay each family member. I should start with Perennia herself. Then I must kill Matthias Draconis in the Talos Plaza District of the Imperial City, Andreas Draconis in the Drunken Dragon Inn, Sibylla Draconis in Muck Valley Cavern and Caelia Draconis in Castle Leyawiin.

After killing all the Draconis family members:
 * Every member of the Draconis family has been killed. I must pick up my reward and next contract at the dead drop located in the stone well in the Castle Skingrad Courtyard.