Well, apart from some issues on Conrad's machine, the English-language 
InstallShield installation of Ruby for Windows is about ready.

http://www.ruby-lang.org/en/raa-list.rhtml?name=Single-step+installation+for+Windows

     A single download that contains everything you need to run Ruby
     under various Windows operating systems. Includes the
     interpreter, the required cygwin DLL, documentation, and Tk
     support. Uses the industry-standard InstallShield system for ease
     of installation. The README file has more details.

This is beta software, so please be careful using it. We recommend
backing-up your registry before installing, and making sure that that
backup works.

Please send feedback to mailto:rubybook / pragmaticprogrammer.com

Hopefully as we get more people testing, we can get the feedback
needed to make this the easiest way for Windows folks to get a running 
Ruby system.


Thanks


Andy and Dave