I think autopick would be way, way easier. Live drafts are tough enough to figure out logistically even when you have all the participants in the same city.
I've done both head-to-head and points leagues. I like both, so I'm all good with either. If I had to choose one, I'd go with head to head.
Are we going to have both a pick 'em and a fantasy league? If so, I'm in for both (unless that's being too greedy, in which case I'd prefer straight fantasy).