I'm doing this from my phone and the search feature is messing up. My questions are when you do raidient assassinations for the Dark Brotherhood and the npc is a named character does the game generate new ones? Say the character is a merchant will it generate a new named one or is that position forever gone?

Bump.

it's a generic generated character. For example, you'll get the contract from the "Shady Agent" and have to kill the "Beautiful Barbarian" and things along those lines.

All the Radient Assassination are generic characters like Zg101 said.

Well I have a guy to kill named anoriath the food stall merchant in whiterun. This is separate contract kill from the main quest line that I'm currently at which is the dark brotherhood forever which is near the end of this faction quest line. If I had to guess I haven't finished the contract quest part for the brotherhood to go to raidient assassinations?