Hey there @Spazierer24087 - great question, and thanks for your topic! 

Firstly, check out our New User Guide - it’ll def prove helpful as you get used to the platform!

Because Calendly sees each account as an individual user, it will not allow overlapping Calendly events in an effort to prevent double bookings. However, we do have a Group event type that will allow multiple invitees to book the same time slot on one event type.

You can also set up a team page that includes multiple users that are actually your alternative email addresses. Then, create a round robin event type between your accounts so invitees can continue scheduling for the same time slot as long as one account has availability. Keep in mind, you will have to pay for each additional user. You can also set up Collective Event Types on a Teams Page - check those out as well! When setting up team scheduling you only have to share the booking link to the teams page to allow invitees to view all booking options for that team in one place. You can also share links to individual events.  

With your specific goal - you would need at least two paid seats on your account so that the overlapping start times can go back and forth between “two” hosts (even if both are actually your own separate email accounts). 

I hope this helps!