Never been to Wiscon, and all things considered, I'll probably never get there, so this is an uninformed comment on many levels. I certainly can't offer any advice.

That being said, I think it sounds really cool. I'm a huge fan of The Moth, and for the same reasons I think your idea is kind of brilliant. I think the people who come to Wiscon would have fascinating stories to tell and it would be an equally good place to find an interested and appreciative audience.

I wonder if five minutes is a little short? And even more, whether sixty seconds for changeover is possibly too optimistic? But my only experience comes from business events where the transition between speakers & topics never happened as smoothly or as quickly as one might anticipate. I'd expect at least two minutes, even in a modest room with a modest crowd... but again, just speculating here.