I've been asked to find a way to improve our phone system in a small office ~10 staff. Asterix has come to my mind because I love open source :) The only thing is that I've heard that asterix is a real b*tch to deal with. I'm not trying to troll, that's just what I heard from (only) two people.
How easy is it to setup a basic asterix system? All we need is extensions and voicemail.
My *nix skillz are not great, pretty basic. Will I be getting in over my head with asterix?

There is a bit of a learning curve, mostly picking up the terms used in phone systems. Start by giving the Asterisk book from O'Reilly a read (free PDF online from the authors: http://www.asteriskdocs.org/).
If it still sounds like something you'd be interested in, then go for it!
Our mailing lists are very responsive and full of friendly people, so I recommend joining them & posting questions there. The forums are a little slow :P