Well, your character isn't defined by their class, thats just their skillset. I'm sure somewhere there is a kleptomaniac priest in TES. =P

Play what you want. If your sig is acurate, it fits with a Nightblade. Thats what Anise is, and despite being Redoran, i'm struggling to decide whether she will Thieves Guild or Fighters Guild in Oblivion. Thieves has the epic final quest and fits her skillset; but being a Fighter is tad more honorable, even if its for hire, and has some character changing moments in the questline.

Do both? If you being in charge of 2 guilds shatters the realism then you always stop the FG questline before the ending, just do the 'thug for hire' contracts and still be DA GRAY FOX111

I think I'll abandon my current Nightblade, start anew. I used random.org, which says I'm a Dunmer Warrior, which sounds really unusual and fun to roleplay.

I could, but i've been planning to give each downloaded companion a Faction questline that they are supposed to have completed.

Dunmer Warrior sounds fun.

Key word here. FG is the easiest guild to join, it's logical that any adventurer would check it out for a quest or two.

I'll try and make the character for real tomorrow, but I've finished the journal introduction!

My name is Mendil Nathius of Ebonheart. I am twenty-nine years old. I am not a traitor.

I know not who, or why you are reading this, only that I likely have been dead for a very long time. I was locked in this cell upon the order of Emperor Uriel Septim VII, on accusations of treachery. I wish it to be known that I am no traitor. I wish for there to be a record of my life, so I am not forgotten. Perhaps, one day, my name will be cleared, and my spirit will rest easy.

I admit I was a criminal. I say this to clear my conscience before I die. Most of my early life was spent on the streets. I have little talent for magic, and learned as a child to improve my physical abilities. Looking back, I have many regrets. I was a foolish bully, beating those who dared mock me. I don’t do that anymore. I have Grandmaster Kallen to thank for that. He and the other Blades rescued me. Took me to Cyrodiil and taught me many great things about the world. They said someday I would learn to fight like them, and join their ranks. I wanted that so much. I wouldn’t have to steal anymore.

Then it all ended so suddenly. I was observing the Emperor’s Court, a temporary servant. How I pleaded to be allowed that job! It all seems so long ago. At first, the Emperor was kind to me. But something happened, something I still don’t understand. I was called before the Emperor, and he called me a traitor. Said I was planning to kill him. I couldn’t believe what was happening. All I remember was being lead here, to this dungeon.

I am to die here. I know it. No guard will come to give me food. The door to my cell does not budge. I hear nothing outside except the distant noises of rats and other foul creatures. The door to my cell keeps me trapped in, but it also keeps those things out. To the outside world, I will have simply vanished. Most likely I will not survive the night. Escape is impossible. I am lucky to have a piece of charcoal in my pocket, and to have found this journal in a dark corner of the cell. Otherwise my entire existence might have been for naught, remembered by none.

I have said my peace. I have lived a short life ended by injustice but I am not sad or bitter. It is my time. It is time for me to say goodbye to the world, to my body, and journey to the gods. It is with acceptance I die.

ONce you get to actually posting your journal entries, (as you've done now) you might want to open a thread in the fan-fic and art section, or once you to daggerfall, in the "what did you do in daggerfall today" thread in Past elder scrolls games.

Awesome idea, thanks!