Well, after two weeks of frustration, I'm admitting defeat. I am not an outliner. I went around in circles on the same plot points. Which isn't to say the experiment was a total loss, in fact I have a rough outline for the next two novels of The Gateway Series, but I was simply unable to move beyond a certain point.
Yesterday I sat down for a long day of writing, and using the notes I'd made, banged out over 2500 words. What seems to work for me is to have a general plot sketch and then let the story evolve as I go. Before I write each scene I plot out what needs to happen in the scene and what the character motivations are, their goals, etc. So I'm essentially outlining, but I can only get so far ahead of myself. I'm reminded of this quote:
"It's like driving a car at night. You never see further than your headlights, but you can make the whole trip that way." ~E.L. Doctorow
Shitty first draft, here I come!