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I was able to edit the transaction file and ran a test by having Barry Bonds traded from the Pirates to the Rangers in 1991. It worked.
Now add that to the fact that rookies can be imported to the correct teams
in 18, i think the the one major obstacle is not allowing automatic transactions before 1901.
If they would allow the automatic transactions before 1901 then Spritze could add the players he mentioned and then we could edit the transaction file and get it to match the schedules. So the not enough players on roster message is avoided. We could also work on settings and if you didnt want to use Spritze's extra players you could block them from the majors or delete them.
We could work on settings for each year. Sure a roster crash may happen but that can still happen in other leagues.
I think it just might work.
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