Here you are. Absolutely amazing work unsure of the dudes tag on here or i would tag him

http://roguesfolio.tumblr.com/Guide

Thank you so much Beardimus. Greatly appreciated. Going to read/watch it now.

So it sounds like you want to roleplay a thief.

Well, the first content I'm going to recommend is the Thieves Guild DLC. Its essential, really, since it adds a lot of depths to the in-game justice system, lets you participate in a whole bunch of capers with a bunch of fellow thieving guildmates, and really gives you the freedom to decide whether or not you want to be a Robin Hood type, a ruthless thief who gradually grows a heart of gold, or a stone-cold robber.

The second thing you'll want to decide on is the Dark Brotherhood DLC. Dark Brotherhood contains another essential element to the Justice system: the Blade of Woe. The Blade of Woe is a one-hit-kill from stealth and is the best way to enhance your thieving and murdering ways. The usual method for maximizing your take from victims is to pickpocket-pickpocket-stab in order to get everything you can from their inventory and reset them quickly. However, if your character has too many scruples to become an assassin, you can pick-pocket your victims three times for the same result, its just much harder to deal with inconvenient witnesses. Even if you choose to be a Dark Brother or Dark Sister, there's plenty of room for character growth.

I like to make up little stories about the places I steal from. In Vulkhel Guard, the temple priests there aren't as pious as you'd think with their pockets filled with Veiled Heritance Codebooks and implements of Daedric worship. Little does the Dominion know I'm doing them a favor by stealing from or killing those priests. And in Morrowind, every noble and commoner my Dark Brotherhood assassin robs and murders is a middle finger to her rivals in the Morag Tong.

Once you've got that groundwork established, its great fun to do other quests with your thief persona. My own Dark Brotherhood Silencer formed a bond with Queen Mariah of the Covenant and now works part-time for her as a troubleshooter and senior agent in the Covenant and if scheming nobles turn up dead with their valuables missing every so often, the Queen looks the other way. Most recently, Divayth Fyr wanted capable help for his journey to the Clockwork City, and well, who's more capably murderous than a Silencer?

So there's the gameplay mechanics of thieving: the lockpicking, the breaking into houses and looting safeboxes, the pickpocketing and the murdering for cool loot to sell. Then there's the content: Thieves Guild and Dark Brotherhood DLCs both add a lot to the Justice system. Finally, there's your character and the stories you want to tell about that character.

Hope you have lots of fun with your thief!