"And you know this rewrite, like others in the past, will be a significant sink of time, and likely a catastrophe." To avoid this establish clear goals for the

"And you know this rewrite, like others in the past, will be a significant sink of time, and likely a catastrophe." To avoid this establish clear goals for the rewrite phase and measure results. Don't just rewrite for the sake of rewriting. Have a session where you identify issues and how to tackle them. From a CTO-Like perspective, getting rid of technical debt should happen frequently, while keeping business goals in mind.