I’ve tried several Linux distributions: Redhat, Coral, Suse, Mandrake, Damn Small Linux, Knoppix, Gentoo and finally Debian. Of all of these I was most loyal to Gentoo because it was the distro I learned the most with. The problem with Gentoo though is you spend so much time getting it to run and tweaking it that you don’t really get to use the machine for what you want to.
For example, I tried and successfully setup a Gentoo desktop on a couple of occasions. But, I will never do it again. I have no desire to spend a week or more building KDE or Gnome when I can have a fully running desktop in less than an hour with other distro.
My main file server is Gentoo and I am leary of updating it. Every time I emerge -u system I have to spend another hour or two cleaning up config files. Then when I reboot the machine I cross my fingers and hope it comes up.
I have started using Debian and so far I like it. Simple to install, apt-get is just as good as emerge and I don’t have to wait days for a compiler to build my system. The plan is to convert the file server to Debian at some point.