A pitcher should work up to the amount of pitches that they will usually throw if they are going to pitch the entire game. That is usually somewhere around 125 pitches. Better to be over prepared than under prepared.
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First off all it would depend on what the score of the game was and how many batters were faced. There is anywhere from 150-300 in a 7 inning softball game. It would depend on the level of play, the skills of the pitchers, and the umps of the game.
They can pitch in any style they want to but it has to be underhanded. It doesn't have to be a windmill, it just has to be underhanded.