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I went through with his file and found that something to do with the actual minor leagues was causing the issue. I could create additional AAA and AA leagues and then move all existing teams with their existing affiliations over to the new AAA and new AA leagues. Then deleting the old AAA and old AA leagues, it would then allow me to sim forward.
The problem is the same crash occurs for his file once I get to the major league preseason date as well. I went through trying to disable a ton of stuff in case something like schedule generation was causing the problem, but no luck it crashed every time.
Someone who has better ability than I at troubleshooting game crashes or digging into the .dat files are going to have to help him on this one I fear.
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