My quest for installation via an USB stick started, but most of the information I found on how to create one was geared towards users that already have Debian or any other Linux distribution already installed.
Read it here
After fiddling with WinImage a bit, I was still unable to properly create a bootable stick. Everything seemed to go ok, until I actually tried booting it. All I got was a unpleasant “Boot Error” on the server, and no installation love at all. Trying to run RawWrite for Windows on Vista x64 didn't yield any better results, as that doesn't even see the USB stick as a device it can write to at all.