Then at some unknown point things slow down in a noticeable way and everyone scrambles to fix the slow down without fixing the culture that lead to it, and that’s if you’re lucky.
Somehow in management eyes rewrites are more palatable than refactors despite costing 10x more
In all of these discussions about reinventing/rewriting/reimplementing already solved x, people forget that other people aren't interested in maintaining something where the fun, education, and impact was already had by the people who came first! They want to have their own fun, education, or impact.
Pretty much every conversation that starts with an angry "this has been a solved problem since such and such genius from the 70's did y" is born from misunderstanding what drives people to do anything.
If you're delivering features quickly it shouldn't matter if you spend some of your time making sure you'll be able to continue doing so in the future.
In part, it is resume-driven development. Rewrites are major projects, and running them (and the associated scale and budget) looks good on a management resume, and provides a nice accomplishment item.
In part, its the short-term incentive to be seen to do more with less, and move on before the consequences bite (this is also a kind of resume-driven motivation, though its more resume-driven development avoidance.) You defer work on anything but visible features, and do those in the quickest/cheapest possible way that will work in the short term, and use the credit for efficiency to move up and out before the deferred maintenance catches up. When it does, someone else gets to do a resume-enhancing big replacement project, since the state of the app makes fixing in place seem impractical. (Ironically, even with deferred maintenance, incremental remediation would probably be quicker, more efficient, and less prone to major timeline and budget-busting surprises, but when it has gotten bad enough, even the technical people who might recognize that will back management’s desire for a complete replacement because they don’t want to have to deal with the legacy mess.)
Because many of them are either incompetents or expect to run to another project or company by the time things start falling apart.