In activation, if you're dealing with more than a couple servers, you've almost certainly got volume licensing and a multiple activation key, which means that your install scripts will automatically update for you. Likewise, installing features like ssh and packaging can be automated as well. A lot of the things that people criticize windows for haven't been true for a long time, especially in the enterprise/service area -- there are a lot of tools out there for making things just as easy, if not easier, than *nix.