Hi – great questions!
When that family arrives, can the check-in person easily & quickly find and check in the whole family in the reporting tool? What does that look like (e.g. can they search by last name?).
The check-in person can whittle the number of entries on the attendee screen down by using a search box, which filters against order number, ticket number or security code.

Also, can WooTickets capture the name and other info (example would be: age, t-shirt size, special dietary concerns) for each ticket sold? In the example of the family, we would need to add this info for each ‘kid’ ticket sold.
Not by itself – but I believe there are a number of WooCommerce extensions that can capture additional information at checkout that you could investigate here, or if not it would certainly be possible with some customization work – it’s a very flexible toolkit indeed 🙂
I hope that answers your questions, but just let me know if I can help with anything else.
Thanks!