Windows is closer to a "Just works" for my use cases. I think if you are more into running applications on a PC or writing software not related to the OS, it can be a good choice. Where I would choose linux for servers, multi-user IT style systems etc.

Windows as a product feels that way, but I think if you're a kernel hacker, that's not really true for you. Monolithic kernels for Unix-like operating systems like GNU/Linux aren't fundamentally that innovative either. (There's innovation within Linux, of course.)

I also don't really think computing advances in such a linear way. Lots of cool new tech is about digging up underappreciated insights from computing's distant past and applying it in a new context, or even just propagating it more widely.

I'm not saying Windows 9x in particular had anything super interesting going on. But all of the viable desktop and server operating systems are based on really old tech, and at the same time computing's distant past is full of hidden treasures.

Please don’t put Mustang and Corvette into the same sentence, they are entirely different classes. Mustang is more comparable to Camaro. While not my cup of tea, the latest mid engine Corvette is a true bargain vs other mid engine performance cars. Speaking of tech, I think the Corvette already 20 years ago had heads up display (projection onto the windshield of current speed).