Windows 95 was pretty much broken “by design”. This is truer than it seems, especially if you skip being charitable by taking the context into account, namely that Microsoft mainly designed Windows 95 for compatibility. (The contemporary Windows NT on the other hand was a much cleaner design, though still questionable above its kernel layer).
You might now ponder whether a broken login screen, i.e. temporarily not being able to access data, is maybe better than downright losing it, but my point was more that I sometimes get the feeling that earlier MS DOS/Windows OSes are now seen through some kind of nostalgia glasses, that seem to make the OSes much more stable and put together than they actually were.
In my experience, most somewhat mainstream OSes were much less shoddy. This includes various Unixes and Unix-likes, but also OS/2 (which was jointly developed by Microsoft, with IBM).