On the other hand, one of the worse ones was the fiasco involving OS/2 2.0, which was much closer to NT than Win9x was and for example could have been used to legally attack DR-DOS. Why did it take 10 years after Intel released the 80386 before 32-bit programming became popular? I have a thread about it here:
http://www.os2museum.com/wp/?p=516&cpage=1#comment-3413