I use Gentoo on my web server, and generally do updates at least once a week. I've probably used Gentoo for ~ 15 years myself, and I do think that the cli-only

I use Gentoo on my web server, and generally do updates at least once a week. I've probably used Gentoo for ~ 15 years myself, and I do think that the cli-only headless setup probably leads to fewer issues than with a full desktop environment. The source-based environment does make it a lot easier to get the latest PHP, nginx, or Postgres.