I was a Windoze (accurate) user until I got sick and tired of the system corruption, viruses, reboots, and being harassed by licensing agreements, registration demands, and having to reinstall it no less than twice in nearly as many days. I still use it for programs that won't run under Linux or have poor support, but in general I use it as little as possible. A friend of mine set up a dual boot (triple boot) system with Lilo: Debian Linux/a second Debian option which apparently uses an older kernel for reasons I don't understand/and WinXP.

He chose Knoppix Debian for me, as I'm entirely new to Linux, Debian has a lot of support, and apt-get makes it easy to upgrade. It didn't work "out of the box" and required a lot of esoteric tweaking, apt-get is currently broken (tried fixing it, I'll post in the Debian forum), and there are a lot of programs I won't ever use. I like Debian, apt-get was great (when it worked), and I have a Linux guru friend for when things go really wrong. However, after reviewing several distros, my heart is set on Gentoo. My friend is warning me against it, and refusing to help if things go wrong. I don't want to have the same mindset I did when I used Windows: My brain lulled to sleep by point-and-click interface, not knowing or understanding what goes on under the hood, and thinking I had to "settle for" Windows because Linux would be "too difficult." I figure I'll learn the most about Linux, and have an optimized system in the process, if I install Gentoo from the ground up. Learning the hard way. I feel like someone learning to read after years of never knowing how, learning a broad concept and world that has been opened to them.

Debian is good, but it is not the distro I would have chosen for myself.

If I installed Gentoo, off a LiveCD, how would I prevent it from obliterating the current Lilo configuration? Windows lives on its own 40G drive, away from Linux, which lives on a 200G drive (16% used.) I don't even know how to safely partition it so that Gentoo has somewhere to be installed. I'm very new, and still set on Gentoo. Linux From Scratch also sounds like something I could learn the innards of Linux from.

I'm determined to one day be entirely Microsoft free.

to prevent it from screwing up ur existing debian lilo configuration, just add another section to it that boots gentoo. you can follow this guide here that teahces you how to install gentoo from an existing linux distro: http://www.gentoo.org/doc/en/altinstall.xml#doc_chap6

if you need support, drop by http://forums.gentoo.org, great support over there