The kernel shouldn't break user space but glibc, Qt, GTK, etc. any upgrade of the most common dependencies will break programs without at least recompiling them.

Windows programs ship with all their necessary libraries and/or link against the Microsoft c++ resist packages and you can have many different versions installed. Your MSI installer has to install the libcurl.3.dll instead of it being shared with other programs.

Docker and Flatpak fix the userland part the kernel part is already stable by "definition". Stuff may still break overtime but no more than it does on MacOS and Window. It's not broken by design anymore.