Hi @joshkimber, I hope that you are well!
Thanks for asking the HubSpot Community and for the context!
For information, here are some articles on the topic:
- Manage recurring billing and payments with subscriptions
- HubSpot payments | Frequently asked questions
I’d love to put you in touch with our Top Experts: Hi @bendonahower, @MrJustinGivens, @danmoyle and @LouiseHare from your experiences, do you have suggestions to help @joshkimber, please?
By the way @joshkimber, I see that you offer educational classes, not sure if you are already using these, but we have a “courses” dataset that might be of interest!
Have a beautiful day and thanks so much for your help! 
Bérangère