I totally agree with tubaman's sentiments, it's the way I've also done things.
I noticed the other day my PC at work actually has a Windows ME key sticker still attached to it, but it's only the case that's 20 years old, actually I do wonder if the power supply is (I'll have to check). I also used Vista, and actually liked it, barely used Windows 8 though, just had that on my laptop.
My older brother certainly worked a lot with DOS, and I used to write machine code on the ZX Spectrum, can't remember when I switched to Windows or what version it was, it was November 1995 I bought my first PC from Mesh Computers (£1566 ouch!) , and I certainly had Windows 95, 98, ME, XP, Vista, 7, 8, and finally 10.
Looking through my MS Money history there's certainly been a lot of money spent on the 'Computer' category over the last 24 years.