Once I spend even the plurality of my time cleaning up messes instead of doing something new (and there are ways to do both), then all the life is sucked out of me and I just have to escape.
Telling me that I have to keep using a tool with known issues that we have to process or patches to fix would be super frustrating. And the more times we stumble over that problem the worse my confirmation bias will be.
Even if the new solution has a bunch of other problems, the set that is making someone unhappy is the one that will cause them to switch teams or quit. This is one area where management is in a tough spot with respect to rewrites.
Rewrites don't often fix many things, but if you suspect they're the only thing between you and massive employee turnover, you're between a rock and a hard place. The product is going to change dramatically, regardless of what decision you make.
