How would you setup an autoresponder series if you're only selling 2 things

Hey guys, in my attempt to achieve my monthly income goal of $3000, I have decided that I need to setup an autoresponder series of emails.

The reason that I didn't do this earlier (I've been at this for a little over a year now) is because I only have 2 things that I'm actually selling. I have a $9 ebook and a $47 course.

Currently, I'm doing around $1000/month in sales, and that is without having an email autoresponder sequence set up. Anyone who signs up to my course automatically gets added to my list.

Anyone who buys my eBook gets a confirmation email inviting them to join my list (most don't click the link though). This is because E-junkie still uses the older "parser" technology, whereas wishlist member (which is what I sell my course through) integrates with aWeber much better.

Then I have my non-buyers who sign up for my list using a sign up form that is on every single page and post of my website. I don't offer a freebie. Rather, I just offer "monthly updates"...every month I just notify them about new video blog posts. Surprisingly, people are still opting in.

Right now I'm approaching a total of almost 500 people on my list, and this is a combination of buyers and non-buyers.

I'd like to really start focusing on this whole list building thing because I believe I have 2 good products. I'm just not sure what the best way to set up an autoresponder sequence would be.

I'm thinking offer a free 5-day mini-course, each of the five days will suggest that they buy my full course. But then what do I do after that? Keep sending them monthly "blog updates" and pitching the course to them?

How do you guys suggest I set this whole auto email sequence up?

Thanks!