My 2 cents on this:
I'm an engineer and armature user of statistics based models in my day to day work for using past data to predict future data (and yes, it is probabilistic as Kim mentioned). To me, this is most certainly "curve fitting" here, or if you don't like that term, he's come up with a model for prediction of profitably playing post-earnings events in TWTR by selling put spreads. The obvious parameters of the model are option expiration, short option delta, long option delta, entry date, and exit date- so 5 parameters.
If he's training that 5-parameter model based on 8 data points (2 years of earnings events), that's n-1 degrees of freedom, or 7 (n-1 since it doesn't include the entire population of earnings events). In analysis of variance (stats 101) for regression modeling, and assuming your errors are normally distributed, you use up one degree of freedom for each parameter, and the rest are left over for calculating error (i.e., confidence intervals for each parameter and error in the overall model).
So, with only 3 degrees of freedom left over for computing confidence intervals, it is very unlikely the interval would be very tight around any one parameter. Hence, that's why I'm very skeptical the confidence interval around entry date is less than +/- 1 day.
So basically, in my opinion, it's wise not to focus too much on the specifics of any one setting CML is predicting based on such a small sample size (as a previous poster mentioned), and just focus on what's actually going on here: implied volatility in the options is in reversion to the mean after earnings announcement to a level that still provides edge over the realized volatility in this time frame, and there's a slight bullish tilt to price (again, for a very small sample size).