Mages and bandits and bears, oh my! Sidequest: Deport Dorothy

Tin Man: The Jarl of Whiterun wants you, yes you! to rid Whiterun of one Uthgerd aka “Dorothy” the Unbroken and clear out a pocket of peril in the southwest corner of the hold.

Seems Dottie has over-stayed her welcome in the Bannered Mare, run up a huge bar tab and bullied one too many well-connected milk-drinkers, so the Jarl wants you to take her and her little dog Toto too, on a quest to secure a vital transportation link (it's a road, and it's paved with yellow bricks) between Whiterun, Markarth and Falkreath.

To be successful you must clear Sunderstone Gorge, Bilegulch Mine and the Moss Mother Cavern, where you will face mages, bandits, bears and worse (yes, worse!). It would also be nice if you would eliminate any giants, mammoths or stray banditos you happen across as part of a general area beautification program.

You may use the Flying Monkey Express to fast-travel to Markarth to pick up Toto, who also answers to “Vigilance,” unless you already happen to have a hound which you can substitute (to be honest, Dot and the dog were never very close); then you should embark on foot from Whiterun so that you don’t miss any chance encounters along the way.

Bonus points if you get the girl and the dog to the Dead Man’s Drink in Falkreath (and convince her to avail herself of their hospitality for awhile, or at least until hot-air balloon travel becomes viable). Mega-props if you complete the quest as the Cowardly Lion (start as an unarmed and unarmored Kayjit, use any potions, jewelry or spells you like and any items you find along the way).

Extra credit if you can present the Jarl with a severed witch’s head and a broom. The whole thing shouldn’t take more than an evening’s entertainment to accomplish, depending on how many side-quests you get involved in (I think the nearest broom is in Fort Sungard Tower).
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One does not just walk into Mordor: not with 10,000 men could you do this thing. However, you could send the Dohvahkin and Lydia; or just Lydia

well, those folks in Sunderstone Gorge do not take kindly to uninvited guests, though they do put on quite a show once the party gets started.

and those giants? i can't figure out why they get so upset over a little thievery; i mean, it's not like they have any use for human sized weapons or armor, right?

fortunately, the Jarl of Falkreath was only to happy to welcome Uthgerd/Dorothy since the boys in his barracks are getting kind of soft and could use a solid punch in the face every now and then.

and it turns out the blacksmith was looking for a dog to call his own so it was a win-win situation for everyone. Now, where's my pot of dwarven oil....
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One does not just walk into Mordor: not with 10,000 men could you do this thing. However, you could send the Dohvahkin and Lydia; or just Lydia