The funny thing is, that we are still on Windows Server 2003 in our company (We run not a single PC, just Linux thin clients that connect to Windows Terminalservers when they need a "Windows-ey" Desktop). We abandoned the move to Server 2008 a few years back, and now are trying to move to Server 2016. The main problems we are running into are compatibility problems between MS products. From what I have experienced there is that it seems Windows stability and comparability is becoming worse.
For example, one problem we are having is that about 50% of the 32bit applications we need don't seem to do name resolution for some obscure reason. Ping works flawlessly, nslookup shows everything in order, 64bit programs don't have any problems, but about a dozen 32bit applications throw "host not found" errors for an unknown reason when they try to connect to their databases / applications servers / etc... using host names. When we replace the hostnames in the configuration with IPs it works.
In my opinion everything before Windows 2000 was not good enough for a corporate environment, Windows 2000 was pretty decent (With the NT Kernel and the "W95 Desktop" experience), and Windows 2003 / 2008 was the peak of Windows Desktops for corporations. (Which would roughly equate to Windows 7 for Workstations)
Which is really a shame. There is nothing that would I like better than have decent current versions of both Windows and Linux.