Hey Matt,
You’ve got a very specific situation that you’ve outlined there. (Nice job on thinking it through!) But I’m afraid that our plugin is a simple calendaring plugin and doesn’t have many of the features you indicated you need. There might be an off-the-shelf solution out there for you, but I’m not familiar with it. To me, what you’ve described sounds like custom work that would require a web developer to implement.
I’m sorry we’re not able to meet your needs. Good luck with your search!
– Julie
(P.S. If you’re want to inquire about developers and what it might cost, you could try contacting WerkPress or The Mighty Mo! to see what they’d say about it.)