Cygwin has all of those things and ssh server support.
<http://www.reddit.com/r/sysadmin/comments/38ba26/professiona...
I ran cygwin-with-ssh heavily for a while in 2003. It was a hell of a thing to get it going. Then I had trouble getting it to work on a new computer and gave up. Shouldn't be surprised that it got good again.
Wait, isn't that nearly everything you ever install on Windows? Not complicated per se, but everything is third party and not signed by people maintaining Windows (as with most GNU/Linux distributions).