I've seen Lotus Notes client installation's folder being migrated from Windows XP to Windows 7 then onto RHEL and finally onto macOS.
Suffice to say that all of the user settings were preserved and the data was readily usable on each platform. This happened over the span of 10 years.
Given the observation, I wonder how many other applications with similar complexity would last even one migration, let alone rolling migration across 4 completely different platforms.