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There are a number of problems with stealing as it relates to machine pitch or coach pitch. For example, when the catcher returns the ball, for the sake of moving the game along it is often returned to the adult who is pitching or running the machine. If that coach misses the ball, can the runners go? If hte machine (or coach) malfunctions and the pitch is wild, do the runners get to steal?
Unless the defensive players have some control over the ball at all times and have the opportunity to put out the runner who is attempting to steal, stealing probably shouldn't be allowed.
If the kids are playing machine pitch, they are likely at the level where they are playing baseball for the purpose of learning the game. I don't like the idea of stealing at that level in a player's development. The catchers can't catch well, they can't throw far enough, accurate enough, and fast enough to have a shot at getting an out, and hte second baseman probaby can't catch a short hop.
Are they learning anything by stealing? If stealing second is so easy it's almost automatic, why not just award second to any player who gets to first?
Players will learn more about the game from having to stay at first and learn about force outs, tagging up, and smart baserunning than they will from getting to second every time because the catcher can't throw the ball that far.
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