Grant - your analysis of how this will play out is correct. (One nit is that everything in here is trading days, not calendar days, but that doesn't change your basic conclusion).
The key question is, on the day the prize is awarded (market close on 2/27), will our calculation be a good/reasonable/fair way to determine the winner? On that day, some entries' scores will be 53% backtest, and some will be 69% backtest, and others everywhere in between (days traded will range from 20 to 33 on 2/27). I think that's going to play out appropriately, but we will see.
The nice part of the backtest component is that it's a longer date range, so a lot of the judging metrics have settled out. The bad part about the backtest is that it's entirely "in sample" and one can tune (curve fit) the algorithm somewhat to get a better score.
The good part about the paper trading component is that it's entirely out of sample and can't be over-fitted. The bad part is that we don't have the patience to wait years to determine a contest winner.
We hope that this formula we are using is a smart blend of the two. We readily admit that this is a bit of an experiment. If we get to February 27 and we don't like the way the leaderboard looks, we will tweak the rules and try again starting on March 2.
So far I'm liking what I'm seeing. It's really early going. The paper trading scores are super noisy - they don't have a lot of days traded (in many cases, just 1 day). Those noisy scores make the papertrading component of limited value. But more days traded means a more valid score, and the weight of them will increase, too.
I will note that looking at last night's numbers, 57 people had a higher rank in paper trading than their backtest, 56 people had a better backtest rank, and 4 people had the same rank in both. It's not clear to me that waiting to the last minute is a good strategy. I think it's more of a roll of the dice. If it turns out that tactics like choosing the right day to enter is impacting the final results, then we definitely will try to adjust the rules to prevent that.
Finally - I second Market's thoughts. I love your contributions.