Hi Cory Trese,
Since the first request eventually arrived but was already expired, while the resent request has not arrived after several hours, this appears to be related to the delivery of the Family Safety purchase notification rather than simply the request not being submitted.
Please check Junk/Spam and email rules, and sign in directly to Microsoft Family Safety with the organizer account to see whether the purchase request is pending there.
If the request appears online but the email notification remains missing, consider contacting Microsoft Support for further account/service-side investigation.
Hope this points you in the right direction.