Hey chrharris,
Thanks for the question. After reviewing your post, it sounds like you want to know about the billing process using Family Sharing. I would recommend that you read this article, it may be able to help you resolve or isolate the issue.
Family Sharing
the family organizer—sets up Family Sharing, invites up to five additional family members, and agrees to pay for any iTunes, iBooks, and App Store purchases they initiate while part of the family group.
Thanks for using Apple Support Communities.
Have a nice day,
Mario