Official comment
Using just PilotPress, you would need to create as many levels as you want to drip out (in this case 40 different levels!) A sequence can then provide access to a contact on a daily or weekly basis.
There are some "Learning Management Systems" our clients are using that can handle this in a different way. You can take a look at the options at our Integration Overview page, and also ask what others are using in our Facebook User Community at https://www.facebook.com/groups/ONTRAPORTusercommunity/ (registration is required if you are not a member of the User Community already).