Is it possible to have QBO automatically generate over 500 bill statement/invoices & print them for customers monthly? Should include balance forward late payment etc.

Good day, @poopandscoop32.

Thank you for visiting the Community space. I can share some information about the recurring transactions in QuickBooks Online.

Currently, the available recurring transactions are Bill, Check, Credit Card Credit, Credit Memo, Deposit, Estimate, Expense, Invoice, Journal Entry, Non-Posting Charge, Non-Posting Credit, Purchase Order, Refund, Sales Receipt, Transfer and Vendor Credit. 

The option to automatically generate bill/ invoice statement is unavailable. You will have to manually create and print the statement. 

We value your willingness to help us improve our products, so I'd recommend submitting this suggestions to our developers. Doing this helps them understand where we can improve and what features should be added so we can better serve you. Just click the Gear icon and choose Feedback.

Let me know if there's anything else I can help you with. I'd be happy to provide more assistance. Wishing you all the best.