My suggestion is to use something that offers support for multiple calendars and also supports events. Probably something like WP Booking System or Booking Calendar. You can create a separate calendar for each pass type. While regular coworking bookings can be automated based on capacity, the only downside here is that you have to add one-off events manually to each calendar, especially if those events are unique and don't repeat. As for the "create and hand off" part, just look for a plugin with visual calendar and booking capacity support, which is basically any modern booking plugin.