If CC offerred a serial autoresponder (which is what you are describing) I would make use of it.
I installed this type of software on a server I own. I had to make some modifications to the PHP code, and sendmail configuration. It is a pain. And it still is not integrated with anything. I need several hundred hours of my time to get full functionality working the way I would like. I'd prefer to just buy it for $35/month as a turnkey application.
I also saw this feature on a competitor's service (Intellicontact). I may use their's, but overall I prefer what CC has much better. Except of course for the lack of a serial autoresponder.
I intend to offer some mini-courses on topics related to my business. A serial autoresponder is what I will need for this. I've only had the CC mail list for about three weeks. I'm still getting my automation started and find CC great for this so far.