What was the hardest quest in vanilla Oblivion?

[Carah]

I got lost in Oblivion getting the great sigil stone. Also, Martin keeped dying on me just after getting in the great gate.

[hbzliln1ck]

i think it would be the last mage quest for sure

[roquefort]

Garridan's Tears was a hard one for me. The tears are hard to spot, and I had to find a cheat map on the web in the end to locate the last one.

 

EDIT: I actually found this quite funny blog thread concerning Garridan and his sodding tears..

http://blogs.ign.com/ShoggIGN/2006/04/12/11395/

[frankc]

Any and all quests with NPC "allies". After countless hours of diligent work I managed to reverse-engineer the AI code for PC allies

 

while (player.isCastingHarmfulSpell OR player.isFiringBow OR player.isSwingingWeapon) {
 jump_in_the_way();
 complain();
}

[LoginToDownload]

I had a huge amount of trouble with the Painted World un-modded. Those trolls could kill me in three or four hits, and I could barely dent them without the turpentine. They could practically regenerate faster than I hurt them. I ended up luring them back to Rythe so they would have someone else to beat on.

[Birrii]

Hmm, I think the most boring ones are where you have to go in a mine and kill everyone. I just hate the environment of the caves and forts.

 

But the hardest one, I think the saving of Darma( the daughter of the owner of the shop in Chorrol). Its not the quest that is hard, it's to get the daughter out of Hackdirt, ALIVE.

When a hackdirt freak starts attacking me, she always starts fighting, and she never stops. She won't run away. And the worst thing is, that the barabarian keeps attacking her, instead of me when I give him a cut with my sword. It's just so annoying.

[Unavi]

I had so much truble with the ogres in the Sins of the Father. The boss ogre was beyond my powers and that time.

It took me several tries and health potions to survive. I had some problems with Lifting tha vale too, but i don't remember why :P

[TheCalliton]

every quest is the hardest if you can tuse the quest lg properly (speaking from experience) i got morrowind once, spent days trying to figure it out

[WrathOfDeadguy]

The entire Fighters' Guild quest line my first few times through the game- I was playing stealth-heavy chars because my comp at the time couldn't handle more than a few enemies in combat at the same time without serious chugging and the occasional crash (any of the Arena fights featuring multiple opponents presented similar problems). I went through a lot of health potions to get my 100% completion, and more than a few CTDs because there just isn't a stealthy way to beat many FG quests. I don't have that problem anymore because my current comp doesn't faint at the mere thought of combat. I still play mostly stealth-heavy characters by preference, but at least they can effectively block and run away now if they have to.

[marabunta5]

The Great Heist is Definatly the Hardest Quest.. first spending 1 hour to find the Entrance in some Maze under the Palace (>.>) then sneaking around (alot) whilst avoiding guards (in the Guard room >.>) then getting some elder scroll from Blind monks (while not speaking to them ) then jumping inside a chimney (dont forget the boots of springheel jack! ) :P