Hey Dustin,
Thank you for your follow-up, but from your reply it’s not clear if the theme itself was tested. We have another report of the Philosophy theme not working well with our plugin, and I cannot recreate your problems, so please try these exact following steps:
1. Deactivate EVERY PLUGIN on your site except for only The Events Calendar, Events Calendar Pro, Event Tickets, Event Tickets Plus, and WooCommerce. If there is any plugin on your site other than just these five, deactivate those plugins.
2. Activate a default theme like Twenty Twelve or Twenty Sixteen.
3. Try those events settings again and see how things behave.
Let us know what you find!
George