This point here doesn't carry much weight: I've been in IT for almost 15 years now as well as supporting family and friends. Almost always, I have to setup the computer to make it easier for them. (MAC, WINODWS, or LINUX) Why, because the average user whether corporate or home can not configure a machine. Those who try usually kill their computers.
Windows is only easier because it's familiar... the above average user to the techie can thrive on linux... I can take anyone who has never worked on a computer and teach them any of the 3 major OS platforms equally.
No amount of careful planning will ever replace dumb luck.