I guess I'm a die hard .. I'm still running Fedora (now Core 6).

I have three headless linux boxes here. Once you do the initial install, you won't generally need keyboards/monitors on these systems. (assuming you can tell the BIOS to not check for a missing keyboard at boot time or not stop if there's a keyboard error). You can use vnc to connect from the windows PC (install Tightvnc on your windows box, activate the vnc server on your linux box). At least with Fedora, after some initial learning about yum, rpm, packages, etc, upgrades from release to release are very easy to do using yum and you don't need heads to do them.

I have a spare (old) ps2 keyboard and mouse in my office and a monitor with two inputs in case I ever need a console to get them booted up. Honestly, I can't remember the last time I needed to connect them to one of the linux boxes. The filesystems are all logging filesystems, so there's very little chance of file system damage even in the event of a power failure.

-David