1. No idea, would depend on timeframe, price of HBD, and the offerings on the DHF at the time.
2. Yes, but not a separate proposal. Put it all in one.
3. Probably 5. 2 runner up rewards for phase one, then 3 prizes for 3 people that make it to phase 2.
4. 2
5. Clear rules. This is the hardest part of any contest, and it's especially hard for something like this. Last time wasn't bad, but if there's anything that could be improved, it's managing expectations. Make it clear what criteria will be judged, and how that criteria will be weighted. Again, easier said than done.
6. No, but I'm sure I'll find some people who would be interested.

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