Chain of fools : Upgrading through every version of Windows [GENERAL TECHNOLOGY]
Andy's Tech Experiments Blog has an excellent video presentation covering an experiment he performed where he which upgraded through every major version of Windows using a virtual machine install. Along with the video installation he has his blog post that offers additional information and details that he did not include within the presentation. Below is the video and his blog post can be found at Andy's Tech Experiments Blog under Chain of fools : Upgrading through every version of Windows