I am still using the same system disk on the Amiga that I used in 1996. I've had some disk to disk copy then when I bought myself new hard drives or had craches,
but that was always a 1:1 copy. Disksalv, quarterback, rdb-recovery, snoopdos and Readme-files is good to have.
I have updated it from 3.0, 3.1, 3.5, 3.9 and gone back some times and have probably tested all tools, patches and apps that is possible to install on this system, well until 2005, it has not been so much activity after this on that computer.
edit: Forgot to say that i have a Directorys dated 1993 of tools on the disk that works well too. It is a kind of tempdir from my A500, but many of the programs work directly from the drawers.
So it's possible, and I do not think this is possible with Windows.