Hey Joakim,
On pondering about my question further, I think one can get "instant" feedback on the 1 year holdout period simply by entering the contest and passing it's contest constraints and threshold tests. I believe Q runs the mandatory latest 25 months backtest for their pass/fail test. If this is correct, then one can see the results of the 1 year holdout period, if it passes the constraints test by running backtest on contest panel. This is under the assumption that Q releases FactSet data on 1 year holdout period when it does it's pass/fail test.
But that said, measurement of overfitting is another matter because of complex considerations like length of holdout period, alpha decay, luck factor, regime changes, etc. Live/real money trading results over time would be the most accurate indicator of overfitting/not overfitting, that is and by itself, a risk even after exhausting all the tools and techniques it applies to OOS data to determine overfitting.