Microsoft's big problem is simply that Windows 7 is quite good. Business desktops use it, they work fine, they crash rarely, and they get the job done. Microsoft conquered the driver quality problem by forcing drivers to pass the Static Driver Verifier, a proof of correctness system which looks at source code to see if it can buffer-overflow, make improper calls, or otherwise crash the kernel. That took care of about half of crashes. The other half, from Microsoft's own code, were handled by a system which classifies core dumps by commonality, so they can collect core dumps with the same cause, then find and fix the problem. So Microsoft conquered the big problem that business cares about - Making It Work.
Businesses see no need to "upgrade". Certainly not to Windows 8. Or Office N+1. It won't help the business.
Microsoft struggles with being "cool". Apple does well with "cool", but nobody else does. It's not clear it will help in the post-Jobs era. (Olivetti once made beautiful office machines. It didn't help them. Most major museums of modern art have some Olivetti products, but few offices did.)
What really made the iPod work was deals with the music industry. Something that many people miss is why Jobs was able to pull that off. Jobs was also CEO of Pixar, and thus, as a major film studio head, at the top of the Hollywood hierarchy. So he was able to deal with the music industry from a position of superiority. That's what made iTunes. (The hierarchy in Hollywood is very real, and very rigid. Ask anybody in the industry.) That's what re-launched Apple. The Mac was below 10% market share, and was stuck there for years, even after Jobs took over again.
There's room for a breakthrough in user interfaces. The rectangular grid of single-purpose icons is lame.
We can be sure that breakthrough will not come from the open source community.