In many modern web companies a given project has a useful life of ~3-5 years, if its still running by year 8 with a team that's been on KTLO a few things are probably true.
A: No one knows how to productively add features.
B: The business need for the project was much larger than the KTLO funding would imply.
Odds are at this point there are a long list of user complaints, year+ old feature requests, and excuses being made to the board for why some initiative is facing yet another delay.
Perhaps we should be talking about software depreciation rather than tech debt?