Hi, Jordan. Thanks for your interest in our plugin suite.
1)
Yes, a single Event may have multiple Organizers assigned to it.
You can test this out in the free/core version of The Events Calendar.
2)
We offer this free extension, which should provide what you’re wanting: https://theeventscalendar.com/extensions/change-labels-events-venues-organizers/
Both of these apply to the free/core version of The Events Calendar. You should try that out and, if you like it, consider upgrading to our paid add-ons.
Last but not least, we have Bundles and a pretty great Refund Policy so you can buy one or many of our add-ons and thoroughly test them.
I hope this info helps. Let me know if you have any follow-up questions.