I think you have your rose colored glasses on. I have nothing to say about MS Bob, but I can certainly attest to Vista and IE6. IE6 was the best web browser in 2001. It supported things like AJAX, which
Netscape Navigator didn't. The fact that you had people using IE6 10 years later, but no one using Netscape Navigator 10 years later should show you that IE was pretty darn good.
Likewise, Vista, for all of its problems, wasn't anywhere near as bad as OS X was in the same time frame. Where Vista had slow file system access and poor video driver support
due to nVidia, it never had the
BSOD issues like Leopard, or glaring
data loss bugs like Snow Leopard did. Actually, for Vista Microsoft re-wrote the entire graphics stack without breaking compatibility.
Last but not least, Microsoft supports their older OS's, and works to
make them backwards compatible*. Something that Apple doesn't care about at all with OS X.
*About 1/2 way down, search for SimCity without the space