As I found out in detail yesterday, extending the system partition of a hard drive is not an easy thing to do! There is a ton of products out there and frankly...none of them seem worth the hassle or price! So I wanted to find a cheap( $0 ) way of doing this. It seems that Windows Server has this lovely diskpart.exe tool. Only thing is, you can't run it on the server you want to "extend". Therefore you have to run it from another server with the drives attached. Now, some of you may not have an all virtual environment like mine, so, you can easily migrate your drives with WinImage. it will create a VPC of your hard drive, then you can "burn" the VPC image to another drive!
What I found out about windows server 2003, it's not so happy with the diskpart command and extending other system volumes. So I tried Server 2008, it worked like a charm! Now I have a 16GB system partition extended to 100GB. Awesome!
Hope that helps people!
Chris