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I'm glad my recommended settings are working out for you. I don't think there would be any problem in setting rotation size to six, even if pitching staffs have fewer than six pitchers. I think five is a reasonably accurate size for a staff in 1901-04. That number would increase to six for 1905-14.
Yes, OOTP can do a much better job of handling pre-reliever pitching staffs than it currently does. And I agree with you that there should be a "never" setting below "very rarely" for closers. Unfortunately, the developers really haven't shown much interest in making even minor changes to this aspect of the game, which is why I've posted my findings and recommendations in the threads that I linked above. Given the limitations of working within the game's rotation model, which is not suited to the way pitchers were actually used prior to around 1940, the best we can do right now is to expand the pitching rotation to encompass as many pitchers on the staff as possible and fiddle with the usage settings.
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