Winnie + Jake's financial situation

Is Winnie supposed to have family money even though her dad went to jail? Are we supposed to think he managed to leave her a lot of money anyway?

They are living in Manhattan is what would - realistically speaking - be a multi million dollar flat.

Shia Labeouf looks 18, but I suppose he's meant to be late twenties or 30 in the film. Still, it does not make sense for him to draw in that much money.
I am aware that the money is meant to be portray what things looked like before th bubble burst and how great the bonuses were. But it was still not the case - or to that extent - with kids his age.
I am not buying him as a "wunderkind" - he just appears like a snotty wiseass to me.
In real life you have to have a Master's Degree to even be an intern at these big prestigious companies. Even if you're talented as hell, you'll be working long hours for low pay while the older guys get the bonuses. On top of it he's supposed to be a moral guy focused on ethics, which let's face it, would never have earned him that kind of money. He's too much of a goodie-two-shoes.
Or is Jake supposed to be from family money with great connections? That's the only way he'd get that kind of job.

Hollywood will always exaggerate, but seriously? Am I missing something here?