Arguably a "complicated mess of cobbled together archaicness" describes most old software, Windows included. I think that's just the nature of how software evolves.

We might be in the middle ages of software development. Think of the way European cities grew naturally versus the grid structures of American cities. Perhaps in the future the art of software development will have progressed to the point where creating a new application results in nice, square lines of code that are perfectly navigable.

I wonder if, at that point, we'll wax nostalgic about the way software used to grow organically. Ahhh, to lose myself once more in the meandering spaghetti of yesteryear...