Controversial idea: Technical debt is something that 'business users' don't need to or want to care about. If you're having conversations about technical debt, you've messed up, and you will continue to have unsatisfactory outcomes until you stop doing so. You can't tell people; here is a dial, you can pick 'fast and you're screwed later' or 'slow and careful now'. You're setting yourself up for failure; they cannot…
Controversial because it's disconnected from reality. You're putting ALL the responsibility on devs as if they are free to present any estimate they like that will then be then accepted without questions or negotation by management. In this fantasy land management is presumably operating in a vacuum with no pressure from customer deadlines, costs, investors, long term product roadmaps etc. I don't know about you but…
Tell Bob I wish him the best of luck in this endeavor, he's clearly a better programmer than I am.