No analogy is perfect, but you’ve got the blackjack scenario all wrong. Taking risks doesn’t mean going all in, ever, it means doubling down with hard 12, or splitting tens, or not hitting a soft 17. Going off book and hoping you get lucky. The reason why you do is that you are almost definitely going to lose if you stick by the book over the long haul.
Anyway, it’s clear you and your dad are committed to sticking to playing by the book, sticking to the chart, believing in the odds to the bitter end.
I disagree. In the postseason, in my opinion, in a short series, the odds mean little. What matters is getting this very decision correct, right now. That means going off book every now and then, taking a risk, going against the odds and hoping you get lucky. We all know that luck already will play a big role in deciding who wins in the playoffs, so you mights as well embrace it, and just go with it.