Is it possible to have features like jigsawbox?

Jigsawbox is basically a limited-feature membership site, but with not much flexibility.
It does this:
Allows a coach to set up a Product which is really a fixed-term membership, and then add modules consisting of text, video, audio etc (ie: a post)
Drip the modules out over whatever period of time the Product membership lasts
Attach a forum to each product

I know so far that's very do-able with just the membership and forum plugins.

The extra bit is that each moduel has a series of questions at the end, and the member can type their answers into the text box, and this allows a conversation between the coach and the member; and the conversation is private.

What woudl be the best way to achieve this, is it even possible?

I'm looking at jigsaw box as an alternative to my own membership site, in some ways it seems easier to have someone else manage all the tech stuff...(though the setup is nearly complete on my membership site). Teh cost is the same as my MU membership and I'd have to do one or the other... I think I'd really prefer to have everythign under my own control. I would appreciate any insight anyone has....

Thanks,

Sandy