Great idea! I like that you give particular suggestions for reading that aren’t inside-EA information sources. Still, though, I would worry that people can quickly read up on the general EA platform and might then expect that toeing the GiveWell line is their best strategy for winning. That would at least get people to think about that information enough to summarize it, which is useful. But it might be useful to explicitly ask for consideration of interventions that differ from any of the major program types recommended by GiveWell/TLYCS/etc.
(I don’t know why this would matter, but it also occurs to me that the most serious contestants are probably reading these comments. Hello!)
You mentioned the separation of parents and offspring, but it’s worth including the effects on the economics of (non-crated) veal production into your considerations. Approximately, each dairy cow is productive for the last three of the five years it is kept alive, and is impregnated once per year to maintain an optimal lactation cycle. source
I’d hypothesize that the overall amount of suffering experienced per day by an adult animal would be less than the amount of suffering experienced by a calf that’s experiencing the stress of separation from its parent. Since they’re slaughtered while still in this state, there could be an even better case for veal calves having lives that are overwhelmingly negative.