Hi @rh7, I hope that you are doing well!
Thanks for asking this question to the Community!
I understand that you’d like to send a recurring email where you’d attach a PDF (which would be the invoice). If that is not the case, please feel free to let me know.
First, I’d like to share these resources on the subject that might be of interest:
- Turn on data privacy settings in your HubSpot account
- Create and manage invoices
I also wanted to invite a couple of subject matter experts to this conversation @karstenkoehler, @Jnix284 and @franksteiner79 do you have suggestions to help @rh7, please?
If anybody else has anything to add and/or share, please feel free to join in the conversation 
Thank you so much 
and have a lovely day!
Best,
Bérangère