Technical debt and its costs are extremely hard to quantify and saying things like "with 3-6 weeks of engineering time we can cut failures in half" is just inventing numbers to get what you want.
A VP of engineering pulled me aside after he saw that one of my proposals wasn’t getting traction and told me “None of the people who are writing alternatives to your proposal are doing the analysis you are, that’s why they look better than yours”
I guess I had never considered that a lot of my peers were just inventing numbers to justify things they wanted and that there’s a careful balance that needs to be struck between “making shit up” and “detailed unbiased analysis”
Let's say person A gives longer estimates but is accurate within 10% more than 95% of the time. Let's say person B gives estimates half as long, but the team runs over by 75% a quarter of the time and by 150% about half the time. Whose proposals should the stakeholders choose?
If your company is making decisions based on estimates, the accuracy trend on those estimates is a far more important metric than lines of code, number of commits, story points, or nearly any other metric they're keeping.
You're probably better off just playing the game and making up good sounding numbers. You're less likely to have half the company resenting you and making your life difficult.
Oh wow. Boy have I been bitten by that before :(
Admit it or not, the reason you want the technical debt addressed is primarily emotional. You are frustrated with how difficult it is to work, you fear for the future of the project. If you want to compel someone in charge to make changes, you need to make them feel things are bad as well.
This is to be used responsibly, though. If it turns out you've convinced someone into acting in a way that is against their interest or a big waste of time, there will probably be blowback later.
It's perfectly rational to be concerned about these things. We are not machines - or rather, we are machines that have mental/psychological/monetary needs that have to be met in the course of our daily employment.
If you explain these logical steps to someone else, what you're doing is showing them that they too will likely be affected by what you're suffering, that is, showing them they have a reason to fear too.
A message's ability to provoke some form of action is entirely dependent on its ability to create some form of emotion, be it fear and indignation or hope and optimism. The most effective rhetoricians are exactly those that are very good at producing those feelings. From Hitler on one side as the archetypal rabble-rouser; to MLK on the other end of the spectrum, who created profound optimism and hope. It isn't because of their syllogisms that they were convincing rhetoricians.
Merely knowing a fact is rarely sufficient to provoke action, unless that knowledge itself creates an emotion (an idea can have aesthetic value, for example).
There's a big difference between "this code is horrific and can't be built upon" vs "ugh, this framework is so old, we need to rewrite it in Foo.js".