I'm interested in "off the grid" living, so I'd like to see some technologies to support that. For example, some good solution to the Internet without depending on expensive telecom companies (e.g. some kind of meshnet, or perhaps land-line based grid that relies on personally-owned routers). Also, can we make home electricity generation cheap and simple enough so that non-experts can figure it out? How about home production of auto fuel, such as ethanol or biodiesel, based on something you can grow in your backyard?
I'd be focused on cheapness, ease of setup, and ease of use with these challenges. Making a windmill more efficient than oil, or ethanol more efficient than gasoline, is not realistic and not necessary to the value proposition of personal independence off the grid.
The vision I have is: being able to have electricity and water, Internet and telephone, without having any monthly bills from utility companies.
I don't know how you'd set the parameters for a contest, or how you'd measure when you've arrived. This kind of lifestyle may be (mostly) possible today, but you'd have to have engineering skills and a lot of free time to make it work.