Maybe going a bit off topic, but I see most automatic or eventual upgrading with OSs being the truly old and definitely inferior versions. But I do not think D&D has really turned out an obviously inferior edition yet. I do not like 1E or 2E, but that is not saying they are inferior, they jsut do not let me do fantasy how I like to do it.
But I know for sure that Win95 Win 98 and WinME are all inferior, clearly inferior to XP and probably Vista. Yes people use them, but they are definitely handicapping themselves.
That is not the case with D&D. Still, it is a good analogy, though