Hi Kristin – great questions!
For your first question, that’s fundamentally more a matter of customizing WooCommerce than it is WooCommerce Tickets, though there’s definitely some crossover between the two. I’d recommend investigating adding custom checkout fields as a pure WooCommerce customization in the first instance – and then looking at how you might further integrate this with WooCommerce Tickets (if that’s even necessary) as a further enhancement. After all, a ticket is, essentially, just a product like any other.
Similarly, your second question really is one that relates to WooCommerce itself. Our plugin has no bearing or influence over the checkout process – so taking these questions across to the team at Woo if you need further insight is probably a good way to proceed.
Hope that helps 🙂