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Destroy the DB: short quest, essentially 'go speak to man, he tells you to go kill the lot of them, you do that'. Moderate reward (I feel like he gives you... maybe 3k septims, not bad early game money, and it's not too hard to kill off the DB as for the most part they are all usually in separate areas of their base) and one word of a Shout, plus an Unusual Gem if you look for it. Can grab a few more freebies such as DB armour, but those are all available to you if you join, as well. I can't remember if you can loot extra sets from the DB members you kill, but I've a feeling you can't.
Join the DB: lengthy questline, generally viewed as one of the better ones in the game. Start off with crappy targets and work your way up to (no spoilers, guys!) a very, very important target indeed. Decent rewards for each quest, unlock a potential very assassin-appropriate spouse (female), and a potential follower who is arguably one of the most entertaining in the game (although he's a bit of a love him or hate him character. He's essential, though, which can be jolly handy if you don't use mods to set followers to essential but like to, you know, not have to keep reloading or finding new followers because the last one jumped in front of your sword.) At the very end you get around 20k which can either be kept, or used to improve the new base of operations which can make a pretty decent player home for assassin types.
As far as roleplaying goes, well, you don't *have* to roleplay a hero. You can roleplay a total arsehole if you want to. You don't *have* to even be the Dragonborn (I mean, technically your character *is* the Dragonborn [there are mods which can disable any evidence of this though such as word walls and dragon soul absorption - not sure if Skyrim Unbound has made it to the Special Edition or not but it's an alternate start mod which lets you have dragons or no dragons and be the Dragonborn (absorb souls/word walls/shout/do the main quest) or not be the Dragonborn (no souls/word walls/shouting/main quest)] BUT if you want you can just avoid handing in the Dragonstone to Farengar in Whiterun and never find out that you are.)
I... it's exactly the same as how to destroy them, you just do as Astrid says in the shack, rather than killing her.
Oh, wait, do you mean the random encounter assassins who attack you? No, that's just random encounters - if you want a hint on how to start the Dark Brotherhood questline (destroy or join) then check your Misc quests for something about 'Aventus Aretino' in Windhelm. If you don't have that, try going to one of the inns, particularly in Windhelm, and asking about rumours. If that doesn't start it, then go to Windhelm and look for a Dark Elf woman speaking to a Nord boy outside a house. Listen to their conversation and then speak to them (her, I think) after they finish talking. This should send you in the right direction.
Oh!! Fair enough. I don't think you can in Morrowind, I think you have to wipe them out or something, IDK, I made the mistake of following that questline in my first game and getting horribly murdered everywhere I went because I was like level two... Still haven't played Tribunal, must remember to get round to that, and Blood Moon...
I made the DB quest, but it was to evil for me, so I reloded.
https://www.youtube.com/watch?v=zBkuNpgACH0
Master alchemy trainer
Immortal horse(that looks the nuts)
Unique player housing
Final quest gives 10k reward.
And it's not just "a longer" questline, it's almost 20 quests in total followed by radiant kill quests. And one of the best storylines in the game.
Where as "destroy" is break into their base kill everyone get their loot +3k.
It's worth doing.
If you're willing to sacrifice that for RP then go for it, but be sure to play through it another time.
If you've never played the DB questline in Skyrim, do it once so you can say you did it. Next time, kill them so you can say you did it.
Otherwise, I avoid it entirely, largely because of the lack of dialogue options on the part of the player when you wake up in the shack.
I mean, EVERYONE in Skyrim knows Aretino is trying to contact the DB. Even the DB knows. You can play the game for 5 game-years and they will ignore him, but as soon as you step in, suddenly you're the bad guy to them and you owe them. What kinda 5h!t is that?