lol...a wonderful analogy :-)
...even among retired internaut friends, they hate Windows and only want to keep Dos...
I love that!
Upgrading from Dictatorship 1.0 to Democracy 2.3 is a big step, no question! But it'll save you no end of headaches in the long run :-)
You've gotta keep the install fully updated, though, or you might see the dreaded message "Your government has performed an illegal operation and will be shut down."
Be sure to reboot at least every 4 - 8 years.