I've been using Gentoo for I think about 15 years (?) now. After uneasy times after the cooler DOS days with the 9x stuff and some alternative stuff (BeOS anyone?) I tried here and there I finally wanted to get away from XP because I felt I wasn't owning my computer anymore with that OS. (little did I know about the horrors of what was to come then) I tried other Linux distributions first, but they had shitty installation scripts and default kernels that would fail on my machine then for various reasons, leaving me completely clueless of what just happened. (I knew nothing about Linux then) Gentoo didn't have tons of hand holding during the installation like they did, but a big installation manual to tell you how to do everything yourself in detail.
I've used other distributions here and there but coming from Gentoo and it's excellent use-flags and way to introduce your own patches into a package (things that only really work well on source-based distros) I found them all to be too inflexible and not giving me enough control over what I have on my computer and running things my way. I also don't feel like being at the whim of package maintainers, and in recent years, the cancer that Red Hat is spreading in FOSS. Gentoo was always good about keeping that stuff out or at least giving you tons of possibilities to whip up your own ebuilds and solutions. In the beginning stuff could break out of nowhere sometimes (and Gentoo also was in a crisis for a while) but in recent years it has been smooth sailing and computers got fast enough that compilation times can be pretty much ignored now, even on (then) low-end, 6+ year old machines. I also only use lightweight, more classical software and avoid bloat where I can. I also don't have stuff like systemd, udev, the various *kits etc. on my systems, that keeps configuration easy.
My window manager when I use X11 is FVWM, I tried tiling ones but I never could get used to them and while maybe efficient, I just find them kinda ugly.
I've been looking at OpenBSD in recent years because I really like their philosophy but their ports collection feels inferior to portage. This got longer than I wanted it to.
