Does anybody know what all goes into determining whether the H/R will be executed? I'm wondering if it is only based on the H/R setting. More to the point, I'm wondering if a pitcher who strikes out every time up will be asked to H/R just as often as more qualified people.

why are you wondering that

Damn good question. I have two teams I'm experimenting with where all players contact rate is above .9, and 4 or 5 good base stealers set on 5. I doubt they are averaging 1 h&r per game. The only time it is done, the outcome seems to be a fielders choice, to stay out of a double play. I expected to see something more dramatic, very minimal usefullness.