Yes, level of play / player skill can be taken into account. After all, ordinary effort for Crystl Bustos is not the same as ordinary effort for little Sally Tenyou.
However, you do need to keep in mind the purpose of the rule - to protect the offense; to allow the runners to stay put on their bases.
Also, in ASA, it is allowed to call the IF after-the-fact and rectify placing players in jeopardy by not calling it. (Although you could expect some lively discussions to follow.)
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Tom
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