Inspiration failed me in the end. But here are the winners:

Into the Black: the winning stories

The top prize went to story where an AI (George) takes it upon itself to redistribute wealth using the concept of collecting the pennies from rounding down numbers in large accounts.
When George finds accounts that have amassed large stockpiles of money, it decides to round down instead of up, and funnel those pennies into a dividend fund. In the end, technology accomplishes what we could not achieve ourselves: a redistribution scheme that holds abusers accountable and ensures no one is left in tears.
If I recall, Office Space used something like that in the plot.

The second story adds a missing person mystery to addressing the surveillance state that would arise from the income distribution.

I'm sorry I wasn't more motivated to finish.