For $50-$100 probably should all go to the winner, but might want to divide it up if you get more responses.
For compelling reasons not to run a cash prize contest, there's a chance people might be discouraged from entering via a low prize (not saying this is the case, just that this is possible). That said, it sounds like an entirely appropriate amount for questions like - "What is the most effective way to run a cash-prize EA essay contest?" as it doesn't require as much effort to write an essay on this topic as on other topics which would require more research.
It also might be the case that the contest needs to be run by someone with high social status or endorsed by an EA organisation in order for people to care about winning.
I have grown interested in the cash-prize EA essay contest format that I've seen on LessWrong. I'm interested in sponsoring a 3-essay series of contests, and would appreciate exploratory thoughts and critique. My goal is to make this essay series produce genuinely useful new information for the community and lead to positive changes in the way we organize these contests. Any strategic advice would be helpful.
The first essay would be on the prompt "What is the most effective way to run a cash-prize EA essay contest? Make sure to specify how winners should be selected and prize money distributed."
The second would implement suggestions from the first contest, and be on the prompt "what is the most compelling argument for not running cash-prize EA essay contests?"
The third would be on the prompt "How could we design a useful scientific experiment to determine the ideal size of essay cash prizes?"
My plan is to offer $50-$100 as cash prizes for each essay. I don't earn a lot by American standards, which is why these prizes are relatively small. I'm considering crowdfunding for higher prizes. I'm not sure if I should allocate it all to the winner or divide it among top posts.
For the second essay, I can determine the winner through the method suggested by the first essay. But for judging the first essay, how should I go about it?