No joke. Around mid 2000's worked at a scientific lab part time. We still had Windows 3.1 machines in there because measurement equipment (sensors) had older DOS based drivers. So would run the experiments then had to use floppies to shuffle results around.
The first Windows-based software I ever shipped was for programming ESC dataloggers. Last I heard, it was still in use by the IEPA Bureau of Air.
http://jalopnik.com/this-ancient-laptop-is-the-only-key-to-t...
AD: Have a look into FreeIPA. It is Active Directory equivalent for Linux and Unix systems (but not Group Policy). Centralized updates are done using Spacewalk/Satellite.
Old stuff: that's the thing with old stuff. Going forward, these things are undergoing a change to web and snmp interfaces. I'm currently looking into thermometers and moisture meters, and this is the standard.
3rd party support contracts: you don't have to accept the stock contract, ask for changes that you need. The providers are not going to say you no, it's just not there because most companies are not asking for it, so they won't be proactive in providing that.
That said, I'm surprised they wouldn't try to support Office via Wine for those users that needed it. Also, for information exchange, the defaults for LO changed to MS Office formats for a given organization... though that still has some issues.
- Office VBA: OpenOffice is good enough for people who just make docs and spreadsheets, but some of the more savvy folk (usually in finance and engineering) use MS Office VBA as a development platform. OpenOffice just doesn't cut it for them.
- Old stuff: Critical sensors, HVAC systems, fuel management systems, etc. that have proprietary windows-only clients. Some work well enough in Wine, others don't.
- 3rd-party support contracts: A lot of places rent their copiers, and even though those copiers have Linux print drivers, the support that is bundled into the contract is windows-only, so you're on your own with Linux.
- AD / Group Policy Deployment: Samba4 is closer, but without windows desktops on the client-end, it's still no substitute for the one-ring-to-control-them-all nature of a bunch of windows boxes under AD, and I'm not just talking SSO.
I think the key-problem with windows is that most users--even in a lot of AD-controlled corporate settings--are full administrators. If you can drop everyone down to limited-user status, it greatly improves things. Not to Linux levels, but still a lot better.