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I think the reason you did not receive any replies before, and may not get much here either, is that you are asking too broad a question. OOTP is very complex, as it has gotten better at modeling the real world of baseball and baseball management. So there are just so many facets to managing a team in OOTP, each of which calls for judgments about good strategies.
You might try breaking the question into smaller parts, and asking more specific questions related to specific strategy decisions you are trying to make.
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