It's going to get easier as I go along, I think. Bits of legal text, rules etc build up over time - I culled much of the SD page from previous contests - and the tasks that need doing as part of a launch become apparent and can be prepared for. For example, I'm putting together a press release about the contest to distribute to game dev news sites (and some gaming sites too, for good measure). It wasn't something I'd originally considered I'd have to do, and I only realised it while preparing to make the contest public. I don't think any of our previous contests have done it, which may explain why we had people only finding out about 4E4 2 months into the contest.
Go on, help me out: Where do you get your gaming/gamedev news? Other than here of course [smile]