"Windows-the-operating-system" is, but "Windows-the-distro" is not. He's specifically mentioning Firefox, so his argument is not restricted to the core operating system.
True, but sometimes those "breaks" are good things (Vista to 7 was nothing but improvement). And generally, Microsoft will support their releases for longer than a decade. XP had over 13 years of extended support, and Windows 7 will have 11 years of extended support. Even Vista, one of the worst OS releases from Microsoft, is still in extended support for another two years.[1]
Contrast that to major (LTS) releases from Ubuntu, which can be from 3 to 5 years, and only 9 to 18 months for non-LTS releases.[2] And Ubuntu is one of the kings of bleeding-edge breakage in the Linux-based OS world, surpassed only by Arch in my experience.
All that said, it's not all rosy in the Windows world, and not all thorns in the Ubuntu world. I just wanted to point out some facts to counter your misinformation.
Not really. The decision to require applications to open ports, as opposed to just bind them, broke pretty much all networked software on Windows in the 00s. That's just one example where software may run but doesn't work. It's complicated.