While installing Drupal on Windows Server 2008 I ran into many issues. Primarily a lot of functions that normally work on a hosted Drupal install do not work on your own server unless they are enabled. In order to enable these features like Mod Rewrite and URL Rewrite I found the fastest and easiest way is to use Microsofts Web Platform Installer
Using 1-click installs Microsoft Web Platform Installer makes it so easy and simple to install Drupal, MySQL, PHP, URL Rewrite, PHP->CGI Script, Fast Cache, etc. Obviously when installing just create a Default website, you do not need to use it as your main site but you can if you want to. The Web Platform Installer will install Acquia Drupal, which is created by the original Drupal team and has a themed installer with its own API for their online suport. It comes with all the views, voting, and other features you may want, but for the master builder who wants to go from the ground up a fresh install of the original Drupal is recommended to a new IIS site. Use the Acquia as a backup of your original site / database.