"Did Microsoft ever really produce reliable software? If they did, I don't seem to remember it. And, I've worked in IT for 27+ years".
We all know the answer to this so no, it is not a revelation.
I cannot say that I've actually worked in IT but I've worked with MS software (at home and at my various professional posts) from 1994 on till three or four years ago when I finally decided to drop it and fully enter the Linux world.
I really have to make an effort to try to recall any long span of time without having some sort of issue with MS software. I recall 3.11 being realtively easy to get around but the most troublesome and hectic was W95. The least troublesome was possibly XPSP3, but that could also be chalked up to accumulated experience.
Just my $0.02.