Wow, what a weird feeling. The authors of this article seem like super smart and experienced guys, but the article itself is introduced with incorrect statements in the very first two sentences and slides downhill from there. "There is a kind of design distortion that happens when a team chooses to build iteratively instead of looking at all of the requirements at once. Ward Cunningham coined the term technical debt…
I would argue that there is the option to look at all the requirements at once. The disconnect with your mental model is in the definition of the piece of software being designed. You’re considering all iterations to be the same piece of software, despite ostensibly having different sets of features and functionality (e.g the ones added over time). Consider the alternative perspective that each new feature actually m…
As a relatable example, think about how the Control Panel in Windows still uses a 2000s-era UI, even as the Settings menu, and most of the rest of the OS, uses a new UI. The likely reason for this is that it was faster to tack on a new UI and leave the Control Panel as-is. It would've taken more time to refactor the Control Panel from the ground up to accomodate a new UI.
The end result is that there are now two separate settings interfaces, and there is probably some ongoing engineering effort required in maintaining both and keeping them coherent with one another. That's a classic example of tech debt - save time now, but it may cost you later.
But, by your definition, the old UI and the new UI are separate pieces of software, therefore there is no debt. How does that track?