Your demo looked excellent and I was looking forward to using SilverStripe for a current project, but after wasting several hours today solving one problem after another I am moving on to something else.
I was trying to install on a Windows 2000 Server that already had Apache 2.2.14, PHP 5.2.11, and MySQL 5.0.51a installed and running a wide variety of other PHP packages live on-line. The first problem was that I had to add "RewriteBase /" to the .htaccess file in the root before I was able to start the installation process. However, that was merely the beginning of a long series of issues.
Eventually I had the "Your version of PHP has defined some classes that conflict with SilverStripe's. The following classes are at fault: HTTPResponse" message others have complained of. It wasn't practical to uninstall the conflicting PHP class, because it is being used by a number of other live websites, so I renamed all instances of "HTTPResponse" to "SSHTTPResponse" as others have had to do, changed the file name. Then after more troubleshooting to discover undocumented file and folder permission issues I received "HttpRequest::__construct() expects at most 3 parameters, 5 given."
The server I was using is configured in a very typical fashion for web serving applications. You obviously either should test to be sure SilverStripe will install and run correctly with a typical installation of Apache and PHP under Windows Server or state clearly that it won't to avoid wasting other people's time. I realize that you recommend use of the Microsoft installation program, but it only works with IIS and there is far more use of Apache than IIS in Windows Server Internet web serving applications.