Yes, an automated mailing service like Lob (YC) would be necessary. Lob takes about 5 minutes to set up and handles all the dirty work of printing + mailing. I

Yes, an automated mailing service like Lob (YC) would be necessary. Lob takes about 5 minutes to set up and handles all the dirty work of printing + mailing. Ideally a user would pay a monthly fee for the extension and then the mailing costs.