Maybe simplicity isn't exactly what I'm talking about, but yes. In fact, I couldn't run your hello world without running my OS. So from a practical point of view, me running your hello world has a dependency on my OS. From that perspective, it's easier for me to run my OS than your hello world.
No, I don't. I have a vague recollection that cygwin was a huge and confusing monolith, but I haven't looked at it in years. This new javascript thing sounded more straight-forward. It's not really objectively supported.