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How much they get a jump depends on the player's speed and pitcher hold. So if your player has a high stealing rating but a low speed rating, he won't go that often, as those players are ones who know where to "pick their spots" but can't simply run on command. If your guy has high speed and high stealing, then he should be able to go most of the time within a couple pitches of an AB.
You can also use the various send forced or hit+run or run+hit options to send them, but obviously they won't have the same success rate.
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