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I was thinking about this today. What are the pros and cons of joining. I could start of.

Pros

Access to poisoned apples (well you could just break into fort farragut but still)
Free enchanted armor and the blade of woe.
Interesting quests and rewards.
The Khajjit merchant has spells costing less magicka than conventional ones.
Easy access to lockpicks. (Khajiit sells them in lots of 30).
Place to hide/sleep/etc.

Cons

Tons of infamy from quests.
The illusion that the members glorify death and murder and that you should not feel guilty doing it. Even though of course it remains criminal. :p
Risk of getting bounties, especially when killing adamus phillida.
Have to kill everyone in the sanctuary at some point, removing interesting npc's
Some quests require you to kill "innocents" ie baenlin was a good guy, sure stuck up but good. His nephew just wanted his house out of greed, and made a deal with the DB to get it. (falling minotaur head)
Francois Motierre is an evil wretch that sacrifices his mother's life so he could live.

I think the pros do outweigh the cons. Mainly because the Dark Brotherhood is one of the most enjoyable questlines (including the best quest in the game, Whodunit?) with great characters. The main downside is that the Dark Brotherhood is kind of evil. It can be hard to justify with a good character, much harder than the Thieves Guild. Suppose you could do it and then have your character redeem themselves. You don't have to be someone who is worshipping Sithis, you could just be doing it for the money. But at the end of the day you are still murdering people for money.

Access to poisoned apples (well you could just break into fort farragut but still)
Free enchanted armor and the blade of woe.
Interesting quests and rewards.
The Khajjit merchant has spells costing less magicka than conventional ones.
Easy access to lockpicks. (Khajiit sells them in lots of 30).
Place to hide/sleep/etc.


--Poisoned apples are difficult/unpredictable to use. I rather use a torture hood (frost goes boom so you know when they put it on/die.)
--A silver dagger is better than the blade of woe, but it has it uses as a training blade.
--Theives guild fences have lock picks x 100
--I think only one of the spells is better than usual, but I don't use restoration spells. The frost+paralyze spell is fun.
--I don't wear light armor other than to build Speed.

I like some of the quests a lot, but the others are very disturbing, and I don't like the idea of worshiping Sithis or being moved "upstairs" to a desk job at the end. And the new crop of murderers are wimpy morons.

The rewards are best after level 30, but I don't need the stuff by then. But the Mother's Blessing can put my numbers over 100.

You can wear the Cowl of Nocturnal when you talk to your controller after a mission and it will take the infamy point from the quest.

Well, pros aside, I've never really bothered about all the cons which is mostly about getting infamy. I'm not worried about getting bounties because if need be, I can provoke the target to attack first, then kill them. Great way to avoid bounties. Other than that, as far as the moral/ethical side of it concerned, its simply a matter of individual conscience. Like the DB saying goes: "Innocence is life's greatest illusion".

As for me, it's all about the roleplay. I had Priestesses, and noble Knights who won't ever go near them. My megalomaniac , sociopathic Wizard considered them too weak, and just turned Lucien into a big pile of ash when he showed up. But I had a lonely, quite sinister Assassin, who found comfortable home in the brotherhood. Well, at least until things started getting nasty with the purification. Then he got depressed, and fell back into his skooma addiction, randomly murdering people under the effects of the drug. After a while he got himself together, and finished the questline.

I think it can work for a redeemed criminal type of character. Do the DB questline, and then go on the pilgrimage from Knights of the Nine to repent and clear your infamy. Then, your character turns over a new leaf and continues on with the rest of the 'good' quests.