Declaring technical debt bankruptcy and requesting a do-over is rarely persuasive, particularly for a profitable service or product. If proponents of technical debt want to win these corner office debates, they need to start developing quantitative models for predicting the size of the debt, and the interest rates. And it may well be impossible, because it's not clear cut that the next design will actually be better. I've seen simple user account management shell scripts replaced with piles of error prone Java, requiring a large set of new DAOs for every new integration.
