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Depends how fast you want to go. Usually, leagues with humans sim a game week at a time, then you can email the league files to your buddy, then you both make what ever moves you want (lineup changes, move around players in the minors, whatever...), he emails his upload file back, then rinse and repeat.
You can go as fast as you want. If you guys can make changes everyday, then you can do it everyday. Most leagues sim 2-4 times/week on average.
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