Hi @makerhacks, you are right in that we could definitely do with more articles on our favourite fruit pie! And it is great that you are offering a very nice incentive for people to contribute to Steemit by taking the initiative.

I have seen and played a few games on Steemit (tried to host some myself too but not quite as successfully), so this is my two cent's worth:

1. Easiest way to track entries seems to be either getting people to reply with comments to a competition post (with answers or links to their posts) or use a unique keyword combination (so you can use @ginabot or steemitworld.org to track entries submitted by participants as posts). Easiest way to judge seems to be by number of upvotes on entries, setting out a specific criteria of judging or using one or more guest judges.
2. I think the most fun thing about a raspberry Pi is doing something or making something with it, so anything to do with coming up with new project ideas or things you have done with it will be fun (but this is not a new idea). But as we grow a community it will lead to some new and interesting ideas.
3. We can and definitely should do this on a regular basis, and hopefully groups like @steemmakers and @thesteemhouse or @steemstem can also help contribute content for this topic so we can grow the community and maybe even create a separate group in the future :)