I have the same problem as you. I want to follow a good path. But I also love the game play of stealth, assassin. And I agree, the Brotherhood quests in oblivion where some of my favourite quests in any game. This is how I solved this dilemma for myself. By adopting the point of view of Thane Krios, the Drell assassin from Mass Effect 2.

Thane: "My employer's killed them. My body was merely the tool they used. If you kill a man with your gun. Do you hold your gun responsible?"

So I'm looking at it from a point of view that I am merely a blade in the hands of the Brotherhood. But of course if there comes an option to where you need to choose a path within a mission, I will do what I think is right.

Another example: In the movie Man on fire, the main character is told (while waiting RPG in hand for the bad guys) that the bible talks about forgiveness. To which he replies: "Forgiveness is between them and God, I am just here to arrange the meeting."

It still hover's in the grey area of morality, but I can live with it. Hope this helps

Being a Jolly roleplayer. I hadn't thought much over my redguard and yet I lacked anyone to enter the brotherhood. For my guy to join was due to his own fears, living in a hell hole where blood and mayhem ran amock. Brought into The nightmare city at a young age his sanity quickly dissappeared and in a last hope tried to fight off his best friend who had already lost her sanity and tried to kill him.
One broken glass peice. Into the heart. She fell part.
Soon the sight of her blood on his hand turn the last notch of sanity he had and turned into a monster. After killing his way to Skyrim for years, he was finally brought down by 7 guards in a bloody skirmish.
He gained abit of sanity during the time, and after breakiing free. He was drawn, towards the wispers of the dark brotherhood. A chance to kill and be rewarded? Where killing is seen as life rather than something to keep? Just like the good old days, in the hell hole that was the nightmare city.

Love that idea. That's what Im doing on my first playthrough.

But after gaining the skills, equipment, and funds I need to be self-sufficient, I will put an end to their organization if I do not like the types of contracts they carry out. But if they are dishing out justice to those who deserve it, I will let them continue doing so.

Being played to kill is a pretty good motive.

you cant be a good character and be in the dark brotherhood, they are just hired mercenaries and kill only in the name of money and fun

I would consider it the will of Sithis and the Night-Mother. Perhaps your character was approached by Sithis in a vision that bestowed upon him the terrible consequences of disobedience. Perhaps your character was abandoned by his family at a young age, and found solace in the dreams bestowed upon him by the Night-Mother. Perhaps your character was betrayed by the Nine Divines and driven to the cold mother's embrace with a promise of justice or vengeance. Perhaps the consequnces of inaction have been forseen to be greater than those of serving the Dark Brotherhood. There are lots of possiblities, but only if they make sense to you. If you can't come up with something, re-do the character, don't join the dark brotherhood, or give yourself a mulligan.

Go with the "Wanted" mind set: Kill one person, to possibly save a thousand more.

Maybe play through the quest not as your "character" but just to experience it just to complete the game more rather than to RP and have it that it was a dream that your character had

Blood money is still good money, sometimes you just gotta crack some skulls to make ends meet.

as "evil" as the Dark brotherhood is for killing people if we look back on the DB targets most of them committed some crime or wronged someone.

It isnt like they just throw a dart at a wall of pictures and say "we will kill this one"

murder is still bad but murdering criminals or other evil people makes it slightly less worse.

so I suppose that could be why we would want to join.

my character is an imperial agent tasked with, among other things, destabilizing the dark brotherhood.

in general i find this is the only way i can reconcile my many odd allegiances.

obviously he would be morally conflicted, but thats just more story material.

Killing everything for fun and profit.

I always play a good aligned character, and know what you mean. I always become a vampire by "mistake" before I join the brotherhood, and blame the new murdering tendencies on bloodlust. When I'm done with the faction, I cure myself of vampirism. Easy enough.

Anyone think there will be multiple sanctuaries and characters in the DB that will be revealed as we continue to play through that particular questline? Personally, my character is seeking justice by infiltrating and ultimately killing all the DB members (in Skyrim at least to cripple operations) he possibly can (especially the leadership). The only problem is, how many innocents do I have to kill to get the names/people I need? Cool character dilemma that makes him walk the line between vengeance and madness I guess, but it's also somewhat vexing for someone who is trying to weigh is options carefully.


EDIT: need to make these bastards non-essential so I can actually kill them. Day 1 mod I guess.

Because you believe that what you're doing is neither bad nor good. You aren't murdering people, you're a tool fulfilling the murderous desires of others. You believe that the Dark Brotherhood is a chaotic force that brings balance to the universe. You believe that there must be opposition in all things, and that the universe is governed by static and chaotic forces, and it doesn't matter which side your on, because they are both fundamental. The Dark Brotherhood is an extension of Sithis or Chaos. Without it, there would be nothing.

You also like money...

haha

My character will be a Morag Tong infiltrator that will be working to destroy them from the inside, Killing will be no qualm as thats what he has been trained to do. To restore the glory of the morag tong.

This.

From an utilitarian perspective that values morals in consequenses and not actions taken, you can easily be a good assassin. Simply kill people for the greater good - meaning using your money to help people out, like feeding orphans and so on. Aslong as the people you kill arent extremely benefactory to the world (most targets seem to be neutral or evil anyway) then the total amount of happiness resulting from this set of cause-effect will make you a morally good character.


EDIT: You can also consider infiltration ofcourse. When you reach the top you can cut off the head of the beast. (Edit: The above idea is ofcourse open to philosophical debate, unfortunately todays moral codes in society are based on actions and not consequenses because of religious contamination, which Im guessing cant be discussed on this forum without being banned)

Model your character after Dexter from the Showtime series. And if you're that into RP then I'm sure you could just not kill someone if you don't think they deserve to die, and then you'd just have the quest sitting in your log.

Join to murder them all i know how find them i will do that quest then once i've ound there base obviously ill be strong enough to do so i will murder them all no killing people for dark reasons.

You answered an ad in the paper.

Politics of course, I hope we can assassinate some important persons this time.

Best answer yet. This is true to the lore about Sithis being the personification of chaos or change. The DB fulfills this by being a destabilizing presence in the established order of things.

Like the Joker in The Dark Knight- you are "an agent of chaos."

he dun [censored]e his pants as a young buck and was laughed at by errone, so he becomes a db assassin to get vengeance on all who utter a chuckle in his presence, but deep down hes a good guy, he just hates the sound of laughter and will kill all who use it willy nilly

Oooh, now that's a GOOD excuse!