To Quench or not to Quench, That is the Question

What's your process for quenching/tempering? Do you just roll the dice as long as you can with quenching and hope for the best (perhaps making multiples of the same tool in case one breaks)? Or do you have a rhythm of quenching and tempering that you abide by?

I typically go for 3 quenches, focusing on durability for tools and damage for weapons.