Hi Dylan,
I can definitely appreciate that that would be a frustrating scenario.
If you visit the Events → Settings → Tickets screen and look at the WooCommerce specific settings, which statuses are enabled both the settings you see there?
new order email – Doesnt work
tickets email – Works
This is strange, but I want to note that the new order email in particular is not something we control – that is entirely handled by WooCommerce itself. If you test this by ordering a ‘regular’ product (ie, something other than a ticket) do you find there are problems with emails then, too?