In addition to requiring an email address, the ability to send an automated email opton for the person to register for Guest membership so we can require a waiver to be done to confirm the reservation.

This goes along with your idea but I would like something like the following.

The ability to turn on or off approve; a member adding other members to their accounts at the membership type level. We have 'Guest/Nonmember' accounts for registering for clinics and swim lessons. We want those members to be able to add without approval

Love this idea. We use WhenIWork because it allows employees to communicate in individual messages or group messages. I would love for an integration to be with a system like WhenIWork. We have a large seasonal staff and they often need to get coverage for shifts!

We are having some issues with the set up of the waitlist as well.
1. Ideally - people are offered registration in the order they signed up but not auto charged. The system we are moving away from would auto send an email to the next person on the waitlist for a camp. You could set the specific amount of time they had to complete registration, then it would go to the next person. 
2. Also, another ideal setting is the ability to have a waitlist but not have space automatically offered. That would allow the admin to choose who to notify. That comes into play for us in several situations, including when a camper is next on the list but they have as sibling also on the waitlist. That allows admins of choose to over enroll to allow the siblings or skip to the next single registration.