...take a risk and attempt to make a big play - knowing that it is low probability but high reward if it pays off. And worst case scenario is 5 yards and replay the down.

The shovel pass was indeed an example of horrible decision-making. The int in the endzone was a bad throw, as was the int on the 2pt conversion. But it didn't "take points off the board". The decision to not kick the extra point is what took points off the board. The 2 pt conversion is less likely to be converted than the kick - it shouldn't be accepted as a given that it would've been points and thus points were taken off the board.

So - I think you're overselling your point. But it is still a point that Jake needs to value maintaining possession over making a play. The shovel pass is the best example of that - live to play another down on the drive.