Very valid issues here. Although it has improved, Windows Update is still shockingly bad compared to any decent package manager used on Linux in the past 10+ years.
I never got into an intractable package issue with windows, where the dependencies were broke in a way where I had to crawl through logs and manually delete things to get them working. That’s happened to me a handful of times with Ubuntu and bad package configs.
I cannot count the number of times that's happened for me on Windows, Linux and macOS. None of them are immune to this problem.