Bill Gates is software's Dr. Death. It doesn't matter what the customer wants; Bill Gates, the richest man in the world, wants more money, and will drag everyone through his neurosis.
Microsoft's business model is to do what hardware manufacturers want. Hardware manufacturers want operating systems that can't run on old computers, so customers will be forced to buy new computers. Sometimes it has seemed to me that Microsoft is not really primarily a software company, but primarily an abuse company that accomplishes abuse through software.
Windows XP was not really stable until Service Pack 2 was released. Before that, Windows XP was full of grief for administrators. Service Pack 2 contained something like 330 documented fixes, if I remember correctly, and I verified that there were fixes that were not documented. Now Microsoft wants people to go through that again??? With a Service Pack 0 release?
Someone said that Microsoft's motto is "The whole world is our beta test site." The entire reason people wanted to migrate away from Windows 98 is that it has an unstable file system, and artificial limits to system resources. Otherwise, many companies would have wanted to stay with their old systems, because employees often run a very limited set of software packages.
Managers in a company that has a virtual monopoly, like Microsoft, may think that the way to make more money is never to release a good product, so that customers will always want more.
Eventually, I think, more and more companies and universities and governments will decide they don't like expensive, stupid, forced upgrade cycles, and will migrate to a managed distribution of Linux like Ubuntu.
The problem with Linux and BSD has always been that developers don't like to document what they have developed. Sometimes user-friendly GUIs and documentation can be 80% of the work, and that work isn't done very well by people who "just want to program".
Linux distributions need a manager like Mark Shuttleworth [markshuttleworth.com] of Ubuntu. Developers don't like to manage their own work, as Mark said he has discovered. The Linux kernel has a manager, Linus Torvalds, and the rest of Linux needs a manager, also.
I have several times offered to help document open source software, but my offer has always been refused. Apparently there is a strong attachment to doing things the old way. Apparently there is a feeling that someone who writes the documentation will get too much credit, even though I did not expect to have my name on what I wrote.
Changing to any new operating system tends to be expensive because of the re-training required. Good top management could help design methods of easing that transition by coordinating the details that tend to be forgotten when no one is really in charge.