640K ought to be enough for anybody. — Bill Gates (well, not really)
It’s inescapable really, you can’t get away. In a moment of immaturity I had major problems with Windows. This was back in they days of 95, 98 and (shudder) ME. I had sparing contact with NT 4, really the first Microsoft OS I had any exposure to was 2000. I grew to love it; it was stable, loved whatever drivers I gave it, and generally did everything I asked of it. XP was an even better refinement of this. Even in the server flavors of 2000 and 2003 I had wonderful experiences. Let’s just agree that Vista never happened, and that 7 just came out years earlier than it did.
I see Active Directory as a great example of a piece of software that works well given the complexities that it is immersed in. Even if it is just glorified LDAP and Kerberos. In a previous position I managed 180 computers and nearly 300 users in a domain. We pushed software updates out over group policy and had full integration with Exchange.
Given my web serving background it was hard to avoid coming into contact with IIS at some point. Dealing with deploying projects using Visual Studio this was, after some cajoling, quite a pleasure to deal with. This all came with the requirement of dealing with MS SQL 2000 for database tasks.