I began IT work on 1995 but not on Windows but on SCO Unix V I maintained the code for an health care organization it lasted me few years then Wincrap beyond any logic become absolutely dominant and distinctly have to learn program this crap (I was entitled on Unix and the original Mac OS), I spent about 8 years on M$ he'll before returning to Unix on the oil industry, my last personal pc running wincrap was an laptop from Hell oops I meant to say Dell, sorry, then I was captured by OSX my first Mac was an iMac with DVD I don't remember now exactly, then I got a MacBook and now I have a mini a nMP and other two iMac one retina one iMac 21 non retina both on my business and my rMBP which mostly is my home computer, plus an 200$ hp laptop I use to experiment on electronics (I'm arduino/raspberry hobbyist and illegal unregistered rebel quad copter pilot/developer lol ), this laptop is dual boot wincrap 10/Ubuntu, sometimes I need wincrap since some flashing tools are windows only.
My current business has little time do with my previous occupations, since I got independent I never programmed or either maintain some system, I keep more less current on OSX programming but since 10yr ago I don't write a line of code for Windows or Linux (except raspberry as hobbyist, don't account as pro).
Hopefully don't need to run again a tool on Windows.