When I was at WAMU, we went from Windows 95 to Windows 2000. When I was at T-Mobile, we migrated straight from Windows 2000 to Windows XP. And Where I am now we went from XP to 7.
IT tends to know when it is worth migrating.
Windows 98, ME and Vista got the cold shoulder. In fact, it really does seem to be an “every other release” sort of thing.
I have a win2k, an xp and a 7 desktop at home. They all still go great regarding what I use them for. The win2k machine is used only for winamp and sonar version 1.3 in a recording studio. No internet.
Windows 98SE was actually pretty good, IMO.