So are these two factions generally done together or should i make separate thief and assassin characters?

I have always used these two guild together it seems sort of fitting to me. In the ragged flaggon you can find members of the dark brotherhood

I did them together because I am a thief/assassin type character.

The thieves guild in Skyrim allows for more killing i think, so yea do them together. IF you want.

You don't necessarily have to be stealthy to be in the DB.

You do if you want to keep your pay, also that reminds me of that orc in the cheydinhal sanctuary in Oblivion, good times.

I like what they did woth the Thieves Guild and the Dark Brotherhood. In the Thieves Guild you weren't allowed to kill your targets and even though they were some sort of a mafia,they still had some very strict rules etc. They seemed to me like knights who beyed the darkness. However the Dark Brotherhood is the opposite, it's madness. The Dark Brotherhood has disobeyed that darkness and they've succumbed to murder and bring dismay to others etc. they are more like Satan in the way that he disobeyed god and got sent to hell and so on. Very, very contrasting factions.

I only do one guild with each character, but I couldn't see it being too far-fetched for a Nightingale to join the Dark Brotherhood.

Well The Companions is designed for warriors, the Thieve's Guild is designed for stealth characters, the College of Winterhold is designed for mages, and the Dark Brotherhood you can choose whatever you want, but you are given bonuses for being stealthy (it is also implied, but there are DB members that try to convince you that a fireball or a mace to the face is better).

Out of all of them I'd say the DB and Thieve's Guild go together the most.

I have leadership over both the "guilds" on the same character.. Its fully doable..


EDIT: Delvin in the thieves guild actually had alot to do with the Brotherhood and Astrid.. So why not you?

Yeah lol good times, I remember that line about not being seen, "who needs a bonus when you have raw skill" and my favourite: "What? You cannot be seen? Screw the bonus, get in there and stab the sick old man" something like this LOL

I usually do them together.

Both with nord warrior. Whats the problem?