I am a rarity in that I essentially had never used any computer platform to any extent until the year 2000. In that year, I taught myself how to use both Windoze and the Macintosh platform. I can say as one of those folks who did not have to "unlearn" anything that the Mac OS is much easier to learn and understand. You do things on a Mac in a way that just makes sense. It works the way my brain works. I found myself saying things that appeared verbatim in the Switcher commercials a few years later. OS X has only made it better and easier. My two cents.
October 17, 1998: System 8.5 Released
July 14, 2002: Apple Previews Jaguar
Best Open Source Software for the Macintosh
The Mac Has Never Been User-Friendly