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I assume you are playing a standard major league setup?
If so. Do you have a minor team in the Dominican League? (DSL) If you do, check to make sure there are no players assigned to it from outside of the Caribbean area. In otherwords, a DSL team can't have any players on it from the USA or Canada as AI will consider them foreigners and will not allow you to advance until you reassign them.
If you don't have a DSL team, then I have no idea what the problem would be.
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