Not much to say for me on details here. Slight connections to Fame and Misfortune. When Twilight made a deal with Iron Will, the problem and likely chain of events was obvious.

They need to take the helm and do what Iron Will had in mind, but their way, through sincerity. A bit of a soft mutiny, maybe. Twilight could still improve her leadership skills there. Maybe get some assertiveness lessons from Fluttershy? (Oh well, as I said, it was predictable that things would turn out that way in the end anyway. Just make sure you apply this awareness to your life, too.) I just found it very unlikely how Twilight could miss the Northern Stars, considering she was looking in their direction, with only the ship's cabin blocking the view.

Lesson: Don't make deals with crooks, but set them straight, set proper standards. That contract wasn't even legit, considering nopony but Twilight's parents signed it. But apart from that, while law is a worthwhile concept, there are higher virtues that trump it. The Dao De Jing puts kindness over justice. The former is more powerful than the latter, i.e. it does not practice justice, yet somehow takes care of its concerns, too.

It is a really good book that I would suggest Twilight to read, so here's the segment from it that I am referring to, from a modern-language version (http://www.beatrice.com/TAO-pamphlet.pdf):

38.
People with integrity
don't even think about it.
That's how you can tell
they have integrity.
Other people talk about
how much integrity they have,
when they really don't have much.
If any.

Truly powerful people
don't do anything,
but they get the job done.
Other people are always busy
doing something,
but nothing ever gets done.

When kind people act,
they do so without thinking about it.
When the just act,
they're always sure
they're doing the right thing.
But when the righteous act,
and nobody reacts,
they try to force everyone
to do things their way.

If you're not in touch with Tao,
at least you can still have integrity.
If you don't have integrity,
there's always kindness.
If you don't have kindness,
there's always justice.
If you don't have justice,
all you have left is righteousness.