Replace a clinic spot - Refund pending someone takes their spot

We have over 400+ clinic spots a week and they all end up with a waitlist. My challenge is this: We do not let the players cancel their spot within 24 hours of the clinic. But say someone knows they won't be able to make it - within 24 hours of the clinic the current system requires them to reach out to me, I manually reach out to each waitlister, wait for them to respond, and then manually swap the players and the charge to let the one who cannot attend off the hook. With over 15,000 clinic spots per year, this is a colossal waste of time for something that can be automated through the software. 

Currently, we could allow players to cancel with less lead time, but they have to be refunded BEFORE someone else takes their spot, which is not guaranteed. I want to have the system allow the player looking to be removed push a button (provisional cancellation pending someone else accepts), then a notification sent to all waitlisters, and when someone "accepts" that spot only THEN the original player is refunded and removed. 

This would save me thousands of hours a year and not impact our revenue negatively. Appreciate it!