Alternative is'nt pain free
I've used MS Windows, and supported it, sold, training etc 1991 to 2004
User 1991 to 2014
There has been some pain moving to Linux Mint + Mate Desktop + WINE, but for me it's far more functional than Win10 (old specialist programs, some have free alternatives on Linux, only costly or no alternative on Win10). OS X seems poorly supported for th stuff I do and a Mac costs too much. Linux runs on all my existing netbook, latop, PC etc.
We changed the server first a few years ago (we quite often had UNIX or Linux on something since 1986) from Windows 2000 (Win 2003 was too bloated for the old Hardware that had been running NT 4.0.) to Debian. Maybe that was 2010.