And all the data in your `~/.config`, `~/.cache` will still be in the old format. Linux programs are notoriously bad at handling that kind of things. There is no local data update api like the one provided by android sdk.
Windows isn't any better. I don't have enough Mac experience but I doubt it has some magic bullet.
now if i'd do that with something that had the original release of winten, probably not. But i'd happily boot a win7 machine that was >3 years offline.