In order to add new life to the game, in which I have over 1000 hours logged, I have decided to embark upon the ultimate Oblivion challenge which is both a fresh playthrough and a nostalgic look at the 5 years Ive spent playing it. The challenge will involve doing the main quest, the 4 guilds, the arena, KOTN and Shivering isles all with the same character. Anyone here tried this?

yup my first character is always about doing everything to do in the game!

Btw: i noticed your signature and i found it funny you are mentioning WWE smackdown you do know WWE is Smackdown and Raw and some other new shows they added recently

All four guilds and both expansions with a single character? Not my style of play, I don't think one character should be able to do everything.

Where exactly does the "challenge" come in?

Will you be adding restrictions, playing dead is dead, anything like that?

Because otherwise I don't really see what the challenge is.

I agree with Callidus. A mage doesn't need to do the fighters guild just like a warrior wouldn't the mages guild.

I have always shied away from this and preferred to role play a character that only devoted themselves to a few things.

Just recently, however, for some strange reason, I have decided to give this a go. Don't ask me why....

My High Elf is about 150 hours in so far-

Thieves Guild (done)

Arena (done)

Mages Guild (the rest of these are yet to do, including MG)

Shivering Isles

Daedra Quests

Dark Brotherhood

Fighters Guild

Main Quest

I doubt whether I will do KOTN. It doesn't really suit his personality.

The plan is to slowly go through them, in say, 900 hours.

i also agree with Callidus i dont see the challenge here

what you are saying is basicly just playing the game :/

My current character is the first I've ever played who is probably capable of "doing everything." She's an impulsive "Chaotic Neutral" free spirit, a kind of female Han Solo in Mithril Armor. She'll keep on doing whatever she does until she dies (I play dead-is-dead) or until she decides to quit.

I don't see "doing everything" as a challenge, but I see it as hard to justify with a single character. If you roleplay, you'll need to come to terms with the character's motivation. As in, why would the same person be a cold-blooded murderer at one time, and a Knight of the Nine at another time?

There are answers to that which work, but I think it's important to at least think about it.