How is this going to go wrong? That's what a pre-mortem is all about. Like a post-mortem analysis, but done ahead of time to anticipate the issues.
My first thought is that this is going to be more complicated than most students are interested in learning without some kind of motivation, carrot or stick. And we are careful about the carrots and sticks, choosing to wield them wisely for only the most important activities.
My second thought ... is happening to me now. I'm worried about losing content that I'm creating. I want to host my own space. Store it in a place I know I won't lose it. Right now I can't get this content to open on another web browser .... have I made it private somehow? Will I lose this is if I close the browser? I need more confidence in the longevity of the product/system. I know my text documents won't go anywhere. Google Docs seem to be sticking around for awhile. I don't know if I can say the same about this. I really can't stand starting to use a new system, because I want all my writing work searchable and in one system. Searching this seem hard. I think this point is about concerns over longevity and access.