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With previous versions, I used to do my import after the season awards were given out but before arbitration and free agency - I didn't like the idea of the new version giving out awards for a season that was played with the old version.
But in more recent versions I do it at the end of the World Series before the offseason starts, simply because so many things happen on Day 1 of the offseason.
The nice thing is that imports copy all of your older version files - they don't get modified. So if you do an import at one point in the season and find you don't like it, go back to the older version, play a little further, and try another import from a new point.
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