There is an Autocratting 101 Compleat Anachronist available through the Stock Clerk that is a good resource.

That aside, I'm a big fan of having co-stewards. The times I've been in that spot, it worked very well...especially if you have one focused on the site/logistics and the other on the people/communication. That and the biggest key is regular communication with the event staff and the hosting group...definitely cuts down on last minute surprises and helps keep momentum up.

The other thing with putting a checklist together is if it's a local event (and if you're mirroring something done in the past or doing something completely new)...or if it's a Kingdom event with a preset structure. The great thing with the Kingdom events is that it does already come with the structure already built in, so you can focus more on the logistics than trying to come up with ideas of things to do. Just need to make sure for Kingdom events that you have the expectations of the Crown (from their chamberlain).