> It’s not that hard to picture people spending 8+ hours a day going through these windows for years if not decades to come, and it’s not hard to add and multiply all...

This is key to being a product manager, as well as a UX designer. It is the single most important lesson to learn for anyone managing stable, longterm software.

I used to be the PM for the Delphi IDE (RAD Studio, C++Builder) and we did a UX refresh. The software needed it, it wasn't arbitrary (there is an old product management joke: if you don't know what to do, do a UX refresh. Same as a CEO: don't know what to do, do an acquisition.) But it was needed, and IMO we did a good job.

This specific view -- that people use our software eight hours a day and we need to respect that through retaining expected behaviour, not arbitrarily moving things, and so much more -- was the guiding principle through that work. Toolbars stayed with the same contents; when settings pages were reorganised, it was with thought and care and we communicated why so that people would understand; UI was more adjusted than redone.

It was not perfect work, but it was done with an attitude of respect for users, and an attitude of minimising surprise. I hope and believe that was visible.

None of it lost functionality like this, which looks like they used an entirely new UI framework under the good. I wouldn't be surprised to hear Photoshop was using some web renderer these days to render their UI.