I was a happy Windows 98 user till my PC developed a life-threatening condition where it had trouble starting up (turned out to be dust inside the case, duh) and I went out and bought a Vista machine. That was 2008. Never had anything to do with ME, 2000, or XP. Imagine my shock when I turned on the new computer for the first time and was confronted with all the UI changes. Took me a couple of years to figure everything out. (I wasn't nearly as computer-literate as I am today. Not that I'm a professional IT guy or anything, but you know what I mean.)
I've come to terms with the fact that with every release of Windows, a non-trivial amount of time must be devoted to hammering the thing back into shape to make it functional again. Windows releases are no longer a matter of excitement but instead it is a matter of preparing for the worst, hoping for the best, (unfortunately with emphasis on worst).
Oh yeah, and the EasyTech kids at Staples had a heck of a time figuring out how to transfer my files from the PATA drive to the new machine. It was like they were looking at some mysterious Etruscan artifact. It took the old guy on their team to know what it was and how to move the information over.