<edited with various clarifications...>
@Sheriff Woody - I am considering helping other fans enter the contest, rather than enter it myself. In the interest of populating 1.0 character adventures, I would like to start a monthly "Trailers to Adventure" YouTube video highlighting seven Toy Boxes each month. In order to be considered for the video, the box would need to have a specific 1.0 character filter and be tailored for that character. Would an entry within one of these goofy videos qualify them for your quarterly contest, provided they also include the INF blocks logo?
Note: the emphasis for each video would be to showcase as many 1.0 characters & as many Disney Infinity Fan contributors as possible, and of course, the ability of Disney Infinity Toy Boxes to tell a story (I realized that numbering the entries would detract from the purpose, so I wouldn't number them). I'd have a DIF logo with the title screen (as a fan member), and would not be directly affiliated with your contest at all. It would simply help with other fans' qualification.
If the Disney Infinity team is amenable to the submissions of 1.0 character adventures, I think we could help out a lot in priming that Community DB prior to the 3.0 launch.