A lot of their platforms (not Azure) used to just work. Visual Studio and .NET were solid. The Windows NT line was pretty good for servers too (but different from Linux, and not as flexible by virtue of not being a bazaar). It was at Windows 8 era they turned it into shit, first by designing a UI for tablets (fine) and then putting that UI on desktops (wtf) and silently upgrading Windows 7 users without their consent.
I remember running IIS and Apache side-by-side many years ago, and oh boy, was IIS a pain.
Instead of a single config dir where you just deploy the configs and you are done, IIS settings were all over the registry. And don't forget component registration - a single, global registry per machine, used by IIS. Want to run staging and dev server on same machine? Tough luck. Random software installs can upgrade components and cause failures in completely unrelated failures...
