From: Near Portland, OR
Microsoft does tend to have problems with every other release of Windows. I thought Windows 95 was pretty good. It was far, far easier to use with the internet than Win 3.1.
I'm a programmer writing programs for Windows and only just upgraded to Win 7 last year from XP. I used Windows 2000 for a long time until it became nonviable and I had to switch to XP. I have no plans to upgrade further until I have to. Win 7 is OK, but I liked XP much better. I used to use Windows Explorer heavily and they utterly broke it to a point where it is unusable in Win 7. I use a third party replacement, which has many more features, but it lacks the simplicity of WE in XP and it's prone to odd behaviors at times.
I'm so old school, I tweak everything to look as much like the Windows 95/NT 4 interface as possible. It was a lot more basic than later interfaces, but I hate learning a new interface. I've learned that it might be related to my mild dyslexia. I have a friend with pretty severe dyslexia and she can have a melt down if someone moves an icon on her desktop. We navigate the world symbolically and based on patterns. When the pattern is changed, it gets very annoying. I have to think through every little step instead of just following the patterns.
For me that's the most annoying thing about OS changes. It is quite possible to build an OS that can be skinned with any interface you want. For example you could have a Windows core OS with an interface that looks and behaves like any previous model of Windows, Mac OS (assuming you got around the intellectual property issues), or any Linux interface. Underneath it would do the same thing, but the user experience could be tailored to whatever worked best for them. Windows Vista, 7 and 8 are actually the same guts underneath. Almost all the changes were in the user interface. Vista got something difficult to use, 7 improved usability, 8 broke it again trying to merge the phone and desktop OS interface, even though they are used very differently.
The desktop OSs are in a difficult spot in their evolution. Personal users are moving heavily over to portable devices, but desktop/laptops are still heavily used in work environments plus personal users who have heavy duty applications (like games too big for a portable device or other CPU intensive or graphics intensive applications). Microsoft has screwed up their OSs trying to chase the personal user market for some years. They have had a good chunk of it through inertia, but Apple has always appealed better to the casual users (personally I can't stand Mac OS, I can't grok it, but it's not made for people who think like I do). Microsoft's strength has always been with business users and they have made their OSs too cutesy trying to appeal to the unsophisticated user base rather than focus on their core customers.
XP was fantastically popular with business users to a point where they extended the end of life much further than they had originally planned. Business has adopted Win 7 to a large degree. The company I work for makes industrial test equipment and they were using XP for their test systems when I started. I had to make changes so their software would work under Win 7, but they plan to stay there until Win 7 become unavailable.
WitP AE - Test team lead, programmer