A Bard's Trials, Day 1

Setup: I know what option it looks like I selected, but trust me, I'm not going to start off drowning.  Perish the thought.  Seriously, the boat is freaking upside down!  I'd never find my way out.

Our story begins with young Leiros, the indolent scion of a wealthy and noble (mixed) family, deciding to go against his father's wishes and attend the Bard's College in Solitude.  Determined to prove that he is capable of making it on his own, Leiros runs away instead of waiting for his courier and bodyguards.
He is promptly attacked and left for dead... somewhere.  He has no idea where he is, and all his belongings are gone.  Upon wandering around for a little while, he comes across a group of Imperial soldiers standing around a few dead bodies.  Leiros, a loyal and civilized citizen, immediately walks up to say hello and perhaps ask for directions.  The soldiers respond by telling him that he is interfering with Imperial business, and that he has to pay 100 septims as a fine.  Fine!
And then Leiros remembers that he is broke, and unarmed.
The guards draw their weapons, and Leiros takes off running at top speed, which isn't very speedy.  However, the advantage of wearing nothing but cheap clothes and serviceable boots instead of full armor rapidly becomes apparent, and Leiros climbs over some rocks and drops down to a different area where the heavily clad soldiers can't follow.  Mindful of the fact that they might just go the long way around, Leiros keeps moving - still completely lost.  And broke.  And unarmed.

This has not been the best day.

After losing the soldiers and resolving never to talk to strange men in Imperial uniform ever again, Leiros decides to climb to the top of a large hill to try and get his bearings.

Yes, right up the hill.

On one side is a mysterious looking cairn of some sort.  Possibly also a mine.  Possibly the mine where the clothes that Leiros is currently wearing came from, but since he's still unarmed and lost, he's not going to investigate.  Meanwhile, to the south, he can see the outlines of some sort of city.  He also realizes at this point that Solitude, where he actually wants to be, is very, very far away.

We're not going there.

At this point, not so much 'lost' as 'abandoned in the wilds to die.'

After a few moments of deliberation (read, 'sobbing in panicked anguish'), Leiros decides to head south towards what should be Markarth.  He hopes.  It's close enough to be reached today, barring attacks by bears, angry soldiers, wolves, giants... (more panicked sobbing)
Realizing that his only hope of arriving anywhere safely is to avoid all encounters, Leiros continues taking advantage of the mountainous terrain, using it in preference to the open plains for as long as possible.  After a few hours of not plummeting to certain death and carefully avoiding wolves and bandits, Leiros comes upon civilization!

A farm!  With people!  And not bandits!

Leiros approaches, and has a chat with the surly owner of Salvius farm.  At least he now knows exactly where he is (at the ass-end of Skyrim) and hopefully can earn enough to get a carriage to take him somewhere that is really civilized.  After checking his pockets - which aren't even really his - Leiros decides to settle for earning enough to eat some dinner and sleep in a bed tonight.  The farmer offers him a simple job picking some potato plants, which Leiros readily accepts.  Because he's desperate   He has 7 septims to his name at the moment.  Leiros has no idea how far that will go in the real world, but he suspects that it won't be enough to buy a horse.

Simple enough.

And so Leiros does some work for the first time in his life.  Note: It sucks.

17 Septims, that's 24 total!

Leiros gleefully collects his wages and continues on towards Markarth stables.  He sees a carriage, and decides to chat with the driver for a bit, before coming right down to business: Getting to Solitude.

Say what?

You have GOT to be kidding me.