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It could be considered that scheduled posts do NOT count towards the cowboy hat prize; it could be a way to "cheat" with them.
Thinking about it a bit more now, I think it could be as you say, and it would save a lot of programming work.
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I like the idea of scheduled posts. I'm not sure an escrow is required though: perhaps it could just be seen as a prepayment. For ease it could be nonrefundable. In that case there is also no need to worry about changing posting fees: the poster just pays the rate at whatever time they schedule the post. Treat cancelling the post the same as deleting a post and it is very simple. Do you think there is a need for refundability?