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I will surprise you by responding to your post, but unfortunately I might not be able to answer your question since I usually play with real players and have not used the simulate multiple years features for a long time. However, I seem to recall that when I was playing about with the multiple years simulation that I had to answer some questions about how the league would operate (including free agency and the draft).
There are still some people who play OOTP5 and you will probably get an answer, but you might need to wait a while. If you haven't done so already, you might want to try searching the website as it is possible that this question has already been asked and answered (I have had some luck doing this).
Good luck and I hope that you are able to figure this one out or get an answer.
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