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I see you say you have turned off the 40 man but to me that and the other roster rules are what have made OOTP challenging
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The 40-man rule, itself, is very challenging. That is essentially the reason why I turn it off.
I feel it is too challenging for the AI to handle.
I play with my own "house-rule" of not breaking the 40-man rule in order to keep the integrity of my roster. However, I found last year that the AI did not utilize it well. I rely on myself to not cheat and take advantage of the AI...but the other AI teams will take advantage of the AI teams that stumble into mistakes with regard to the 40 man rule.
Hence....this is why I turn it off. To attempt to protect the AI from itself.
I rely on myself, as you do, to keep the integrity of the game high on my end, personally. Thanks for your explanation and I may test the 40-man setting to see how well the AI handles it now.