[NS] Have all five daddies ever played side-by-side for another DM?
And if they haven't, might I suggest Will's sister? The more he talks about how often he turns to her for ideas and advice, the more convinced I am she'd be an amazing DM, especially for the daddies. It would be a treat-and-a-half to see (hear) her run all five of them through a one-shot or mini-series.
Just, y'know, putting that out into the world in case, y'know, the world is ever looking for Patreon content ideas...