I wonder at what point a refactoring becomes just a waste of time and money compared to a slow rewrite. It becomes difficult to have an adult discussion about the subject, but obviously it's about money and how clients don't have a choice.
https://neilonsoftware.com/difficult-people-on-software-proj...
There are softwares out there that are just waiting to be put out of their misery, until another savior company finally builds a viable replacement.
At some point it becomes a true crisis of faith, "is it realistically possible to get work done at this job, and should I be okay earning money by mopping the rain".
Of course those softwares are out there, but I can imagine young engineers are not always aware of what is out there.