I kinda feel like this is better for folks who've been at it for a little bit. There are way too many distros claiming to be beginner friendly for a tool like this to be helpful.

I think it's better to just send them to an easy to install, up to date distro that will suit their needs that has a DE that's easy to understand but different enough from where they're coming from to keep them from expecting it to work like windows. Stable updates from a GUI, software availability, and easy to use backup tools are all a plus.

Which OS am I talking about? Hell, I have no idea. Fedora? Maybe Vanilla 2 when it comes out? Certainly nothing Arch based (sorry, guys, I love arch too but it's not for beginners...).