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> There's also a weird opposite myth that old software is bad, and urgently needs to be rewritten with newer paradigms.

Some of the challenges with old software is the ecosystem around it. Is the language it's written in still supported on modern OS? (Visual FoxPro for example). Is the database it's using still around? What about the libraries? Are they tied to a certain runtime version with no update path? Do you even have access to the source code for these dependencies? Or the application itself? Can it build on a recent machine?

I've seen projects where some infrastructure around an old piece of code was re-written to make it run on modern platforms, but that takes good engineering (some assembly required) that companies often simply can't afford.