Oblivion:Roleplaying/Holy Agent

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A Holy Assassin is an assassin who kills the sinful, and you don't have to be religious to have fun! Its kind of like the assassins in Assassins' Creed.

First make a custom class labeled Holy Agent or Holy Assassin.
Look for characters who worship Sithis or the Night Mother or Mehrunes Dagon.
You could kill every killable member of the Thieves Guild without joining.
To leave a personal touch, use a wide-ranged fire spell to wreck the houses of your victims.
Download the unofficial mod "Hashshashin armor" for a nice touch (if you want).
You may want to use a mask mod to hide your identity.
Pray in the evenings for forgiveness.
Roleplay a monk or Blade (or anything if you want) after you kill someone to let the commotion die down.
You could kill someone plotting a major attack on a city (use your imagination).
Remember, you don't do this for money.
When you kill someone lay their body down peacefully, then sprint away for an escape.
The Temple of Ancestor Moths is a nice place to lay low since it is far out of sight. Cloud Ruler Temple is good too.
If you join the Fighter's Guild, kill Cirroc after the Stone of St. Alessia quest. He isn't worthy to protect the Stone as he already lost it once.
Plan your escape before you plan your kill.
Kill who you must, no more.
Only loot the bodies if it's essential.
Learn your victim's schedule.
If you have access to consoles and mods, you can kill essential characters (with the mods) and bring them back to life afterwards (again with mods), just pretend they don't exist.
If you're going for the Assassin's Creed kind of assassin, it doesn't hurt to act like Altair (Social stealth, jump off a building with a certain hidden blade to your enemies throat, etc.)
If you do not have hashshashin armor mod use use white monk robe and grey hood with leather boots.