That's generally not supported and will require manual interactions.
Periodically, some upgrades of some packages do require manual interaction when configured in certain ways. However, this is usually a general issue with a change in packaging which isn't actually any more onerous for systems that hadn't been updated in a long time.
Now, it's true that every once in a blue moon something really big does change. The big one I remember was updating a system that had been shut down for some years, and the compression used by pacman had changed in the meantime. That one did require some self-imposed manual intervention :)
If I have problems during the process, it's almost always a signing keys problem. Package verification fails because too much time's passed between updates: the keys stored on my computer are too old and don't work anymore. I made a script to refresh the keys and everything started working perfectly.
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.