There is middle ground between doing significant changes all the time and no changes in ~30 years.
I was working at a software company years back that was doing this significant interface change. I suggested we have an 'end goal' interface and breakdown changes into multiple releases over time, organised it so each version change is easier to adapt to and educates somewhat in the changes as they occur, but this approach got no traction. I still wonder if its the correct approach or its better to get it over with in one go and then try to be stable.
At least in my experience the “one and done” feels better, but make it so the new one is somehow faster or easier or something. (Not salesforce lightning, e.g.)
The other ends up feeling like death by a thousand cuts.
