I'm going to go for Windows 10 when it comes out; I have Windows 8.1 at work (so I'm used to it now), but it is one of those things where you wish you could have 'skipped' the "bad" generation. I hear they are reasons they called it "Windows 10", however, in the past.....
In DOS days, even versions of their OS were considered 'bad'. DOS 3.3 was the best, but 4.0 (from a source) ate the date on hard drives. 5.0 was awesome, but 6.0 had issues, the 6.2 had to step it up a bit.
Windows 3.1 was the best of its time too. Windows then decided to go by years.... 95, it was a great thing, Windows 98, not so highly accepted and Windows Millenium was like throwing something out in left field.
Windows NT was still active at the time and converging (funny how they are melding 'all' Windows into one), and Windows NT 3.51 was pretty solid while NT 4.0 with the Workspace shell was getting close to what was becoming Windows 2000.
Windows XP seemed to be that melding of the two, and Windows 2000 with Service Pack 6 was probably the closest thing to XP.
Windows Vista seemed to be a train wreck and they had to save that one by releasing Windows 7 ( a version I currently use and really like), until a bunch of Metro artists decided to turn it into their own art project and start melding it with tablets.
Thus came Windows 8 and 8.1 and 8.1 updates, it worked great for people who liked to touch their screen (for tablets, that's a given), but for monitors, I don't like looking through grubby fingerprints. I think they dropped the ball on the workflow between the 'desktop' and the 'tablet' user and they didn't really go through all the usability testing for desktop users.
Now we have Windows 10, I think they learned their lesson, it's a better hybrid of what they had and more friendly for tablet and desktop users. However, will your legacy software run on Windows 10?
Just as 16-bit Windows applications don't seemingly run on 32-bit Windows systems anymore, there may come a day when 32-bit applications won't run on 64-bit Windows. This is kind of the "move up, or move out" strategy one has to deal with in order to make sure their software can be ported and still working on new systems.
Sad, but true.