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Last time I tried was when it was still called RedHat. Generally you stick the CD in and go through some screens and then pick "WORKSTATION" or "SERVER" and then you wait 40 minutes and then it "works" (for lack of a better term). It was all GUI. You could probably do it without having a keyboard plugged in.
RHL, Fedora Core2, and SuSE are the only distros I have used so far. If I had more time, I would set up slackware box as I generally hate the GUI. (I like runlevel 3 and BASH. :D )
I hate slackware :p Debian and Gentoo work nicely for GUI-less systems for me. I've just finished setting up a headless gentoo box with only SSHD and Samba running on it, and I do everything I need to over SSH to it.
The "screen" package is quite handy in this situation too, since it means I only need a single SSH session/window into the box, yet have multiple bash sessions in the one window. Plus I can disconnect screen and close the SSH session, then SSH in from elsewhere and reconnect screen and continue where I left off - anything running in screen continues running instead of dying if my connection to the machine dies :p
SSH is just one of the coolest things since sliced bread... :D