I am trying to do the very same thing. Seems like a pretty standard way to layout a site map. I'm a Visio user trying out OmniGraffle to use at home on other projects. I'm impressed and really like it so far, except for this issue, which is a deal-breaker for me. With all the other great things it can do I'd really be surprised if it can't take the outline and lay it out vertically (or side by side). Love to hear an answer on this...