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The Ides of March competition seems like a great idea. As it says, it will encourage donations and promote interest in textkit.
But why wait until March? Surely it would be better to have more regular smaller competitions? How about essay/article competitions? These would stimulate interest even more, and rapidly increase textkit's content. One of the problems seems to be getting to people to visit the site regularly. I think this would help a lot. Competitions could be on any topic; a simple essay title; a translation.. etc. The best titles would be "open" titles because then everyone's entry could be put on the website (rather than having 20 discussions of why they like Greek or whatever...).
Contests should be scarce since they will accumulate much anticipation; more frequent ones may be taken for granted. Creative classics-related contests, perhaps judged by experts, would offer so much more than prizes.