I'm currently plotting a WIP with a character who basically spends the entire book making increasingly poor decisions. Essentially, the backstory is this: after her parents were convicted of fraud, she lost her entire college fund, and turns to several unorthodox and eventually illegal ways of making money in order to steer her future back on track. It's nothing involving alcohol, drugs, or firearms, but she's definitely not a morally upstanding citizen - she has no qualms about lying, cheating, helping others cheat, or making fake IDs. But when you have a character like this in a YA story, they typically have to lose, get in major trouble, or otherwise learn their lesson at the end.
So my question is... is this absolutely necessary? In the majority of heist films and gangster movies, your heroes may do morally questionable things, but you root for them, and they typically get away scot-free or with a slap on the wrist at the end. Can a complex, interesting YA hero/ine do the same? I'm interested in hearing both sides of this issue, because I really can't figure out where I want this plot to end up.