In reverse order. I certainly support people learning their legal rights in any situation including bankruptcy. However, you should know that personal bankruptcy now involves (since 2005) credit counselling. It would not make this debt go away, only add it to the pile.
As to a judge... I learned long ago not to predict judges even on someone clearly one-sided. Some contracts require you to go to mediation first. Of course that is more their recourse than yours. All you have to do is withdraw your child from school. I would hope that a judge would decide based on what is fair but this is a contract issue and the first remedy is according to the contract.
If you want to proceed you might consider how publicity would look. Does this school really care about their students if they go this far to force a family to pay their tuition? I can imagine that such a publicity war would cost them more than this is worth.