Earlier quoted context omitted.
> I think mostly where it goes awry in the wild is people forgetting the paying it off part. Which also fits the financial debt analogy perfectly.
What would bankruptcy be analogous to... the business going under? Having to rewrite the application due to unmaintainable code?
Still if you really want to take the analogy further declaring technical bankruptcy could cause business bankruptcy (see Joel Spolsky). You probably want to refinance your debt and get onto a repayment plan (an incremental rewrite) instead.