Not needing to reinstall at all, is one of the nice things with linux. Just upgrade now and then - for years and years. An upgrade normally "just works" and you don't have to re-do any customizations.

And in the rare occations when there is some trouble, just paste the error message into google and find how to fix it.

DLL Hell?
Debian seems to get this right - using package dependencies.

Upgrading an app may pull in a new version of some library. This, in turn, pulls in newer versions of 15 other apps using the same library. So the upgrade got bigger than expected, but it works.