Hey Tia,
Currently, there is no option for an Automation to be sent out a year after the product is sold for a reminder in re-purchasing their product.
As for the Offline Pricing Plan payments, the best way to work around this would be to generate an create an invoice or recurring invoice manually, to help assist this process. There is no email that is automatically sent out as a reminder.
I understand the importance of this feature and will be forwarding your feedback to our product teams. #PricingPlans #Stores