girldetective's on the right track, I think.
I've never done a film festival, but I have been involved in arranging various live events.
A lot of it varies by region I think, so advice that I can give for doing stuff in Ontario, Canada may not necessarily apply to Seattle, USA.
First order of business is to contact the city hall. You'll need to make sure you're square with any and all city ordinances, and you'll probably need a permit of some description. If you plan on serving alcoholic drinks, you might need a special permit for that, and there may be extra rules to follow.
You'll also need to contact the venue if you haven't already, and find out what the expenses are. Then there's advertising and so on, which from what I know of you I'm sure you'll have well in hand.
The biggest thing, though, will be securing rights for all the different films you want to show. Honestly, web shorts are probably your best bet. If you contact the producers you can probably secure viewing rights on the cheap, where something from a major studio might be more expensive. A lawyer versed in contract law will be crucial for this step to make sure all the t's are crossed and i's are dotted. Last thing you want is to get a lawsuit out of this.
It's a lot of work, but I'm sure you're up to the challenge. Best get started now.
A thought just crossed my mind -- have you contacted the PAX people about this? Machinima is growing fast, and you'll have an audience practically ready-made as it is. That might be something worth investigating. Perhaps if you agreed to donate part of the proceeds to Child's Play, they'd be open to the possibility of some cross-promotion. Can't hurt to inquire, at the very least.
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I wake up in the morning more tired than before I slept
I get through cryin' and I'm sadder than before I wept
I get through thinkin' now, and the thoughts have left my head
I get through speakin' and I can't remember, not a word that I said
- Ben Harper, Show Me A Little Shame
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