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I think that once you handle the basics (how the game is played), the biggest challenge may be to decide who you want to put on your team. Are doubles important? How do I know if a pitcher is good or not? Evaluating players (and the understanding of statistics and their respective importance) is probably the next step. Glossaries can probably help you with that, and so will books, but careful not to start with sabermetrics, which are in-depth analysis of baseball statistics, because they are very abstract and are more meaningful if you have understood the basics first.
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