I used Gentoo for a while and mostly liked it. There was one reason I stopped using it -- dependency conflicts. Every time you update, there's a new set of conflicts that you have to personally untangle.

By any other metric, I would consider it more user-friendly than average. For example, I was very favorably impressed when (not knowing what I was doing), I gave the command to uninstall libc, and after confirming that I really wanted to do that, I was allowed to.