Okay so I was in my mid teens with my imperial paladin character who I'm RPing she was sent from Cyrodiil to skyrim to recover all of the daedric artifacts and dragon priest mask so they can't be used against the empire. (plan on learning all the shouts with her too)

So anyway I'm going down the road and Cicero is standing there, his wagon wheel broken. I was shocked. I played over 1000 hrs easily and never came across this. He was very friendly to me and seeing as my paladin had no clue this funny jester was in the dark brotherhood, I decided to convince the local farmer with my relatively good (high 20s by that point) Speech skill to help the strange fellow out.

So yeah, every time I think I've done everything in this game, I eventually come across something new.

True, every time I think I have done everything I find an Inn or a mine that has people with quests.

I had something similar happen last night as well.
This is quoted from my thread last night:

"So I was in Riften training in smithing with Balimund. I dropped a bunch of stuff on the ground to clear my inventory so I could organize everything I had... Well, that kinda caused the town to break out into a riot. I first dropped a potion by accident and that beggar Edda ran up to me asking if she could have it. I was pretty amazed to see that, I thought, well, now that's really neat of the AI to do that. So I started dropping my other stuff, armor, bars, weapons, etc. Well, Edda and that other beggar fought to the death over some of my stuff, something about "Seeing it first" A guard scolded me for dropping a weapon, as that was dangerous, what with children around and what not. And a few people kept asking for my stuff XD Oh what a mess that was. I had no idea the AI did things like that. Then again, I've never dropped anything in town before. A good 1000 hours in, and still finding stuff out every day. This game amazes me.

Anyone else have something like this happen? Or something astounding? The only other "Wow moment" I can think of, was when I was being attacked by an assassin and a group of thugs all the while Alduin was resurrecting a dragon in the background, creepy clouds, swirling draconic magic, dragon speak and all."

ive never seen that im kinda jealous

It is at a farm north of Whiterun. Can't remember the name though.

I've never encountered him so far, but then again I never completed DB-questline so I didn't meet him there either.
But as I say: "There's enough time for everything, no need to rush."

Oh I have no plan to do the DB quests with this character, she's a paladin. He was literally broke down in the middle of the road. Like a poster said before me, its north of whiterun.

http://www.uesp.net/wiki/Skyrim:Loreius_Farm

Rent a room and spend the night in every single Inn in Skyrim. Sometimes you'll be rewarded in unexpected ways, like on the ship in the Imperial City in Oblivion.

Had something similar happen to me at the timber mill west of Windhelm. I was heading to speak with Ulfric, and a dragon attacked the mill as I passed through it. After the battle and subsequent soul-theft commentary, I looted the dragon for bones and scales. Well, the weight was such that it would slow me down, so I dropped a few things from inventory, intending to come back to see if they were still there. After I dropped everything, one of the workers eyed me warily and said, "You know, that might not be there when you come back..." I blinked a few times, then smiled. When I came back, it was all gone except the crappy stuff, and the workers were all avoiiding me. Hehehe.

Just remembered, a couple of days ago I was messing around waiting for shops to open in Whiterun. Picked up the bucket by the well to put it ON the well, but wound up just dropping it. One of the townies came over, picked it up, and handed it to me. "Oh, dearie, you dropped this. You'll want to be more careful." Second time I put it on the well and left quickly. Sheesh.

Scenarios like this is why I don't fast travel much anymore. I used to ALWAYS fast travel with my main, but you miss out on so much in the world. It's so much better when you just wander and see what you find in the world.

What happens when you do that?