A summary of my Windows-related experience:
always had some sort of MS-DOS or Windows PC in my home as my main personal workstation, and was a power-user of it, from early 90's through say 2007 (MS-DOS 3.x/5.x, Win 3.1/95/98/XP). Still have a Win XP/SP2 laptop I use to test Windows ports or for Windows-only apps (*tears*)
done simple .BAT scripting
done autoexec.bat configuration (driver loading, memory config, etc.)
did a gig as a tech support specialist in early 90's for Windows (helping customers with issues, troubleshooting network/app configuration & connectivity)
wrote 2 Windows games in C/C++ using the Borland GUI API's (early 90's)
did C++ COM/DCOM programming with VC++ in the mid-90's
used CygWin and wrote apps using CygWin gcc and dependent on that runtime
written C/OpenGL apps for Windows (War Command and Imperium)
a Java-based Windows game of mine, Shattered Stars, was accepted for publication by Manifesto Games (I did all of the design, coding, and Windows packing of it)
written a Python/PyGame app for Windows (Ganymede)
ported my Python/curses-based Dead By Zombie standalone game from Mac to Windows and launched it in July 2009