I agree with above, it all depends on what environment you're in. Gentoo would be suitable for some but not all servers, but if you want a Linux server as secure as it can be, or specifically set up, then I find it does automate things well. It gives you a decent amount of choice, the stable branch is tested and stable, and it's easy to change on a per package or global basis, but compiling isn't practical on all systems, neither is setting up your own binary repo (you could obviously compile for generic but at the same time you could not compile at all). The configuration settings can be updated easily with a command, and most things do come with sane defaults, but I think things should be configured 100% properly beforehand anyway. I don't have experience with larger servers but I think its good for small and easier to manage ones.