Worse is Worse negates the aspects that purity in the vacuum is very pure and very useless. There is (extreme) value in network effects, and network effects also exists in technology, not only in social networks... (and well, in technical fields, both are related). Also it's extremely easy to keep only good memories of extinct systems, and remain focused on past defaults, that for the most part have been largely corrected or at least compensated by dozen of years of refinement on still alive systems.
I don't negate that there are some technical choices that are better than others in some context, or even in some cases in every aspects. But e.g. the PC loser-ing problem has in practice hardly caused much problems (and is even in some cases a superior approach even for the userspace), and judging systems by that kind of details can easily be compared to an hypothetical crazy mechanical engineer not buying a car because of an obscur mechanical technical detail in the engine, that has been made to work perfectly well by taking into account its peculiarities, but that he dislike by principle and in an absolute way.
I'm also very aware of the enormously costly impact of some de facto industry choices. For ex: the C language and its derivative are shit and have arguably costed an absurd amount to the human kind -- compared to a technological-fiction world where safer languages would have been used. Does that mean that this is a case of "Worse is better"? Maybe, but then what would it mean? We have processors with MMU, we even have IOMMU that are becoming more and more common. Given some existing software stacks this does not need to be an intrinsically requirement -- but IMO this is vastly better. Can Worse sometimes win, and then Better also win on other subjects? What should we deduce from that then? What insight can we extract? If none, this whole categorization would be meaningless.
So in some cases, "Worse" is actually just better, the "worse" in question only being in the eyes of the opponent. Or you need to be extremely precise about the criterion you are using.
But I prefer to stick to consider all the advantages and drawbacks of what I'm talking about, the situation I want to apply it to, and avoid binary categorizations when they have no predictive value.