I’m extremely excited about this.
For the past, um, very long time I’ve been working on a plugin for YNAB (3.0 and later only) that lets you schedule common inflows, outflows, and budget items one time. You then just click a button once per month and those items are automatically entered into the Register and Budget automatically.
I’m very excited about offering something that lots of YNAB users have been asking about. Head here for info on the Scheduler Plugin
UPDATE: The Scheduler is being slowly phased out. If you’re looking for the ability to automate your entries, I would suggest you look closely at YNAB Pro.