However, he wants to make it a monthly fee and pretty much automated.
The simplest thing I could think of without going the Clickbank route yet was a PayPal subscription and automate via Aweber.
Aweber can send out a video lesson for that month to customers provided they stay a member.
If the customer decides to cancel from the lesson, they can quit PayPal easy enough.
But what about Aweber? What if they forget to unsubscribe? That means they'd be getting lessons for free. I don't think my friend would want that.
It's not certain that this is the methodology he will choose, but if it is, I'd be interested in knowing how to make Aweber and PayPal simultaneous with one another, if at all possible.